diff --git a/Makefile b/Makefile
index 7ab38cccb5..e52a003964 100644
--- a/Makefile
+++ b/Makefile
@@ -1355,9 +1355,10 @@ docs/reference/cli/index.md: node_modules/.installed examples/examples.gen.json
 		mkdir -p "$$tmpdir/docs/reference/cli" && \
 		cp docs/manifest.json "$$tmpdir/docs/manifest.json" && \
 		CI=true DOCS_DIR="$$tmpdir/docs" _gen/bin/clidocgen && \
-		pnpm exec markdownlint-cli2 --fix "$$tmpdir/docs/reference/cli/*.md" && \
-		pnpm exec markdown-table-formatter "$$tmpdir/docs/reference/cli/*.md" && \
-		for f in "$$tmpdir/docs/reference/cli/"*.md; do mv "$$f" "docs/reference/cli/$$(basename "$$f")"; done && \
+		pnpm exec markdownlint-cli2 --fix "$$tmpdir/docs/reference/cli/**/*.md" && \
+		pnpm exec markdown-table-formatter "$$tmpdir/docs/reference/cli/**/*.md" && \
+		rm -rf docs/reference/cli && \
+		mv "$$tmpdir/docs/reference/cli" docs/reference/cli && \
 		rm -rf "$$tmpdir"
 
 docs/admin/security/audit-logs.md: node_modules/.installed coderd/database/querier.go scripts/auditdocgen/main.go enterprise/audit/table.go coderd/rbac/object_gen.go | _gen _gen/bin/auditdocgen
@@ -1404,11 +1405,14 @@ coderd/apidoc/.gen: \
 		rm -rf "$$tmpdir" "$$swagtmp"
 	touch "$@"
 
-docs/manifest.json: site/node_modules/.installed coderd/apidoc/.gen docs/reference/cli/index.md | _gen
-	tmpdir=$$(mktemp -d -p _gen) && tmpfile=$$(realpath "$$tmpdir")/$(notdir $@) && \
-		cp _gen/manifest-staging.json "$$tmpfile" && \
-		./scripts/biome_format.sh "$$tmpfile" && \
-		mv "$$tmpfile" "$@" && rm -rf "$$tmpdir"
+# The API doc rule stages the manifest with its section rebuilt; clidocgen then
+# rebuilds the "Command Line" section on top of it so both land in the tree.
+docs/manifest.json: site/node_modules/.installed coderd/apidoc/.gen docs/reference/cli/index.md _gen/bin/clidocgen | _gen
+	tmpdir=$$(mktemp -d -p _gen) && tmpdir=$$(realpath "$$tmpdir") && \
+		cp _gen/manifest-staging.json "$$tmpdir/manifest.json" && \
+		CI=true DOCS_DIR="$$tmpdir" _gen/bin/clidocgen -manifest-only && \
+		./scripts/biome_format.sh "$$tmpdir/manifest.json" && \
+		mv "$$tmpdir/manifest.json" "$@" && rm -rf "$$tmpdir"
 
 coderd/apidoc/swagger.json: site/node_modules/.installed coderd/apidoc/.gen
 	touch "$@"
diff --git a/docs/admin/external-auth/index.md b/docs/admin/external-auth/index.md
index 938427c7ef..290fa03c63 100644
--- a/docs/admin/external-auth/index.md
+++ b/docs/admin/external-auth/index.md
@@ -88,7 +88,7 @@ Reference the documentation for your chosen provider for more information on how
 
 ### Workspace CLI
 
-Use [`external-auth`](../../reference/cli/external-auth.md) in the Coder CLI to access a token within the workspace:
+Use [`external-auth`](../../reference/cli/external-auth/index.md) in the Coder CLI to access a token within the workspace:
 
 ```sh
 coder external-auth access-token <USER_DEFINED_ID>
diff --git a/docs/admin/integrations/devcontainers/envbuilder/add-envbuilder.md b/docs/admin/integrations/devcontainers/envbuilder/add-envbuilder.md
index c520bef492..89e17df4a0 100644
--- a/docs/admin/integrations/devcontainers/envbuilder/add-envbuilder.md
+++ b/docs/admin/integrations/devcontainers/envbuilder/add-envbuilder.md
@@ -32,7 +32,7 @@ choose a template from the
    ```
 
    A list of available templates is shown in the
-   [templates_init](../../../../reference/cli/templates.md) reference.
+   [templates_init](../../../../reference/cli/templates/index.md) reference.
 
 1. `cd` into the directory and push the template to your Coder deployment:
 
diff --git a/docs/admin/integrations/dx-data-cloud.md b/docs/admin/integrations/dx-data-cloud.md
index a1ccbd05c5..358329e505 100644
--- a/docs/admin/integrations/dx-data-cloud.md
+++ b/docs/admin/integrations/dx-data-cloud.md
@@ -39,7 +39,7 @@ coder users list --output json | \
   jq -r '["username","email","created_at","status"], (.[] | [.username, .email, .created_at, .status]) | @csv' > users.csv
 ```
 
-Visit the [users list](../../reference/cli/users_list.md) documentation for more options.
+Visit the [users list](../../reference/cli/users/list.md) documentation for more options.
 
 ### API
 
@@ -85,6 +85,6 @@ After the attribute is uploaded, you'll have a Coder filter option within your D
 ## Related Resources
 
 - [DX Data Cloud Documentation](https://docs.getdx.com/)
-- [Coder CLI](../../reference/cli/users.md)
+- [Coder CLI](../../reference/cli/users/index.md)
 - [Coder API](../../reference/api/users.md)
 - [PlatformX Integration](./platformx.md)
diff --git a/docs/admin/monitoring/connection-logs.md b/docs/admin/monitoring/connection-logs.md
index 9e7c9514a1..60f07afc88 100644
--- a/docs/admin/monitoring/connection-logs.md
+++ b/docs/admin/monitoring/connection-logs.md
@@ -91,7 +91,7 @@ for details.
 Connection events are also dispatched as service logs and can be captured and
 categorized using any log management tool such as [Splunk](https://splunk.com).
 
-Example of a [JSON formatted](../../reference/cli/server.md#--log-json)
+Example of a [JSON formatted](../../reference/cli/server/index.md#--log-json)
 connection log entry, when an SSH connection is made:
 
 ```json
@@ -124,7 +124,7 @@ connection log entry, when an SSH connection is made:
 }
 ```
 
-Example of a [human readable](../../reference/cli/server.md#--log-human)
+Example of a [human readable](../../reference/cli/server/index.md#--log-human)
 connection log entry, when `code-server` is opened:
 
 ```console
diff --git a/docs/admin/monitoring/health-check.md b/docs/admin/monitoring/health-check.md
index 3198521cb1..816d80ae19 100644
--- a/docs/admin/monitoring/health-check.md
+++ b/docs/admin/monitoring/health-check.md
@@ -111,7 +111,7 @@ query fails.
 #### Database Latency High
 
 **Problem:** This code is returned if the median latency is higher than the
-[configured threshold](../../reference/cli/server.md#--health-check-threshold-database).
+[configured threshold](../../reference/cli/server/index.md#--health-check-threshold-database).
 This may not be an error as such, but is an indication of a potential issue.
 
 **Solution:** Investigate the sizing of the configured database with regard to
@@ -121,9 +121,9 @@ configured threshold to a higher value (this will not address the root cause).
 
 > [!TIP]
 > You can enable
-> [detailed database metrics](../../reference/cli/server.md#--prometheus-collect-db-metrics)
+> [detailed database metrics](../../reference/cli/server/index.md#--prometheus-collect-db-metrics)
 > in Coder's Prometheus endpoint. If you have
-> [tracing enabled](../../reference/cli/server.md#--trace), these traces may also
+> [tracing enabled](../../reference/cli/server/index.md#--trace), these traces may also
 > contain useful information regarding Coder's database activity.
 
 ## DERP
@@ -131,7 +131,7 @@ configured threshold to a higher value (this will not address the root cause).
 Coder workspace agents may use
 [DERP (Designated Encrypted Relay for Packets)](https://tailscale.com/blog/how-tailscale-works/#encrypted-tcp-relays-derp)
 to communicate with Coder. This requires connectivity to a number of configured
-[DERP servers](../../reference/cli/server.md#--derp-config-path) which are used
+[DERP servers](../../reference/cli/server/index.md#--derp-config-path) which are used
 to relay traffic between Coder and workspace agents. Coder periodically queries
 the health of its configured DERP servers and may return one or more of the
 following:
@@ -151,7 +151,7 @@ still be able to reach their workspaces, connection performance may be degraded.
 
 > [!NOTE]
 > This may also be shown if you have
-> [forced websocket connections for DERP](../../reference/cli/server.md#--derp-force-websockets).
+> [forced websocket connections for DERP](../../reference/cli/server/index.md#--derp-force-websockets).
 
 **Solution:** ensure that any proxies you use allow connection upgrade with the
 `Upgrade: derp` header.
@@ -203,7 +203,7 @@ to establish [direct connections](../networking/stun.md). Without at least one
 working STUN server, direct connections may not be possible.
 
 **Solution:** Ensure that the
-[configured STUN severs](../../reference/cli/server.md#--derp-server-stun-addresses)
+[configured STUN severs](../../reference/cli/server/index.md#--derp-server-stun-addresses)
 are reachable from Coder and that UDP traffic can be sent/received on the
 configured port.
 
@@ -317,7 +317,7 @@ be built until there is at least one provisioner daemon running.
 If you are using
 [External Provisioner Daemons](../../install/operate/provisioners/index.md), ensure
 that they are able to successfully connect to Coder. Otherwise, ensure
-[`--provisioner-daemons`](../../reference/cli/server.md#--provisioner-daemons)
+[`--provisioner-daemons`](../../reference/cli/server/index.md#--provisioner-daemons)
 is set to a value greater than 0.
 
 > [!NOTE]
diff --git a/docs/admin/monitoring/logs.md b/docs/admin/monitoring/logs.md
index 31061056c8..e4800d0429 100644
--- a/docs/admin/monitoring/logs.md
+++ b/docs/admin/monitoring/logs.md
@@ -15,11 +15,11 @@ on Kubernetes or `journalctl -u coder` if you deployed Coder on a host
 machine/VM.
 
 - To change the log format/location, you can set
-  [`CODER_LOGGING_HUMAN`](../../reference/cli/server.md#--log-human) and
-  [`CODER_LOGGING_JSON`](../../reference/cli/server.md#--log-json) server config.
+  [`CODER_LOGGING_HUMAN`](../../reference/cli/server/index.md#--log-human) and
+  [`CODER_LOGGING_JSON`](../../reference/cli/server/index.md#--log-json) server config.
   options.
 - To only display certain types of logs, use
-  the[`CODER_LOG_FILTER`](../../reference/cli/server.md#-l---log-filter) server
+  the[`CODER_LOG_FILTER`](../../reference/cli/server/index.md#-l---log-filter) server
   config. Using `.*` will result in the `DEBUG` log level being used.
 
 > [!NOTE]
@@ -33,7 +33,7 @@ Connect logs are all captured in the `coderd` logs.
 ## `provisionerd` Logs
 
 Logs for [external provisioners](../../install/operate/provisioners/index.md) are structured
-[and configured](../../reference/cli/provisioner_start.md#--log-human) similarly
+[and configured](../../reference/cli/provisioner/start.md#--log-human) similarly
 to `coderd` logs. Use these logs to troubleshoot and monitor the Terraform
 operations behind workspaces and templates.
 
diff --git a/docs/admin/monitoring/notifications/index.md b/docs/admin/monitoring/notifications/index.md
index af7f2f54a2..5cf745525f 100644
--- a/docs/admin/monitoring/notifications/index.md
+++ b/docs/admin/monitoring/notifications/index.md
@@ -67,10 +67,10 @@ OOM/OOD notifications can be delivered to users in VS Code.
 You can configure:
 
 - SMTP or webhooks globally with
-[`CODER_NOTIFICATIONS_METHOD`](../../../reference/cli/server.md#--notifications-method)
+[`CODER_NOTIFICATIONS_METHOD`](../../../reference/cli/server/index.md#--notifications-method)
 (default: `smtp`).
 - Coder dashboard Inbox with
-[`CODER_NOTIFICATIONS_INBOX_ENABLED`](../../../reference/cli/server.md#--notifications-inbox-enabled)
+[`CODER_NOTIFICATIONS_INBOX_ENABLED`](../../../reference/cli/server/index.md#--notifications-inbox-enabled)
 (default: `true`).
 
 Premium customers can configure which method to use for each of the supported
@@ -274,7 +274,7 @@ Custom notifications let you send an ad‑hoc notification to yourself using the
 These are useful for surfacing the result of long-running tasks or important state changes.
 At this time, custom notifications can only be sent to the user making the request.
 
-To send a custom notification, execute [`coder notifications custom <title> <message>`](../../../reference/cli/notifications_custom.md).
+To send a custom notification, execute [`coder notifications custom <title> <message>`](../../../reference/cli/notifications/custom.md).
 
 <!-- TODO(ssncferreira): Update when sending custom notifications to multiple users/roles is supported.
 	 Explain deduplication behaviour for multiple users/roles.
@@ -311,10 +311,10 @@ Administrators may wish to stop _all_ notifications across the deployment. We
 support a killswitch in the CLI for these cases.
 
 To pause sending notifications, execute
-[`coder notifications pause`](../../../reference/cli/notifications_pause.md).
+[`coder notifications pause`](../../../reference/cli/notifications/pause.md).
 
 To resume sending notifications, execute
-[`coder notifications resume`](../../../reference/cli/notifications_resume.md).
+[`coder notifications resume`](../../../reference/cli/notifications/resume.md).
 
 ## Troubleshooting
 
diff --git a/docs/admin/networking/index.md b/docs/admin/networking/index.md
index 9179b65516..a85d12035f 100644
--- a/docs/admin/networking/index.md
+++ b/docs/admin/networking/index.md
@@ -52,7 +52,7 @@ In order for clients to be able to establish direct connections:
   communicate with each other using their locally assigned IP addresses, then a
   direct connection can be established immediately. Otherwise, the client and
   agent will contact
-  [the configured STUN servers](../../reference/cli/server.md#--derp-server-stun-addresses)
+  [the configured STUN servers](../../reference/cli/server/index.md#--derp-server-stun-addresses)
   to try and determine which `ip:port` can be used to communicate with their
   counterpart. See [STUN and NAT](./stun.md) for more details on how this
   process works.
@@ -60,7 +60,7 @@ In order for clients to be able to establish direct connections:
   **all ports** to each others' respective networks.
   - To establish a direct connection, both agent and client use STUN. This
     involves sending UDP packets outbound on `udp/3478` to the configured
-    [STUN server](../../reference/cli/server.md#--derp-server-stun-addresses).
+    [STUN server](../../reference/cli/server/index.md#--derp-server-stun-addresses).
     If either the agent or the client are unable to send and receive UDP packets
     to a STUN server, then direct connections will not be possible.
   - Both agents and clients will then establish a
@@ -115,7 +115,7 @@ for more information on how this process works.
 
 If a direct connection is not available (e.g. client or server is behind NAT),
 Coder will use a relayed connection. By default,
-[Coder uses Google's public STUN server](../../reference/cli/server.md#--derp-server-stun-addresses),
+[Coder uses Google's public STUN server](../../reference/cli/server/index.md#--derp-server-stun-addresses),
 but this can be disabled or changed for
 [Air-gapped deployments](../../install/prepare/airgap.md).
 
diff --git a/docs/admin/networking/troubleshooting.md b/docs/admin/networking/troubleshooting.md
index 78a607c745..b884aaf8d0 100644
--- a/docs/admin/networking/troubleshooting.md
+++ b/docs/admin/networking/troubleshooting.md
@@ -115,7 +115,7 @@ disable direct connections and relay all traffic via DERP instead, which
 will not be affected by the low MTU.
 
 To disable direct connections, set the
-[`--block-direct-connections`](../../reference/cli/server.md#--block-direct-connections)
+[`--block-direct-connections`](../../reference/cli/server/index.md#--block-direct-connections)
 flag or `CODER_BLOCK_DIRECT` environment variable on the control plane.
 
 ## Throughput
diff --git a/docs/admin/networking/wildcard-access-url.md b/docs/admin/networking/wildcard-access-url.md
index b818484585..3fc50b4a15 100644
--- a/docs/admin/networking/wildcard-access-url.md
+++ b/docs/admin/networking/wildcard-access-url.md
@@ -76,7 +76,7 @@ Use a reverse proxy to handle TLS termination with automatic certificate managem
 
 If your reverse proxy rewrites the request `Host` and forwards the original
 host in `X-Forwarded-Host`, configure
-[`CODER_PROXY_TRUSTED_ORIGINS`](../../reference/cli/server.md#--proxy-trusted-origins)
+[`CODER_PROXY_TRUSTED_ORIGINS`](../../reference/cli/server/index.md#--proxy-trusted-origins)
 to trust that proxy's address. Otherwise Coder will ignore `X-Forwarded-Host`
 for subdomain app routing.
 
diff --git a/docs/admin/security/audit-logs.md b/docs/admin/security/audit-logs.md
index d0af66ca7d..eb80a463c4 100644
--- a/docs/admin/security/audit-logs.md
+++ b/docs/admin/security/audit-logs.md
@@ -98,7 +98,7 @@ for details.
 Audit trails are also dispatched as service logs and can be captured and
 categorized using any log management tool such as [Splunk](https://splunk.com).
 
-Example of a [JSON formatted](../../reference/cli/server.md#--log-json) audit
+Example of a [JSON formatted](../../reference/cli/server/index.md#--log-json) audit
 log entry:
 
 ```json
@@ -134,7 +134,7 @@ log entry:
 }
 ```
 
-Example of a [human readable](../../reference/cli/server.md#--log-human) audit
+Example of a [human readable](../../reference/cli/server/index.md#--log-human) audit
 log entry:
 
 ```console
diff --git a/docs/admin/security/database-encryption.md b/docs/admin/security/database-encryption.md
index 6e3f770646..778dc80134 100644
--- a/docs/admin/security/database-encryption.md
+++ b/docs/admin/security/database-encryption.md
@@ -10,7 +10,7 @@ reading or misusing them.
 ## How it works
 
 Coder allows administrators to specify
-[external token encryption keys](../../reference/cli/server.md#--external-token-encryption-keys).
+[external token encryption keys](../../reference/cli/server/index.md#--external-token-encryption-keys).
 If configured, Coder will use these keys to encrypt external user tokens before
 storing them in the database. The encryption algorithm used is AES-256-GCM with
 a 32-byte key length.
@@ -59,7 +59,7 @@ values using that key to a new key.
 
 - Ensure you have a valid backup of your database. **Do not skip this step.** If
   you are using the built-in PostgreSQL database, you can run
-  [`coder server postgres-builtin-url`](../../reference/cli/server_postgres-builtin-url.md)
+  [`coder server postgres-builtin-url`](../../reference/cli/server/postgres-builtin-url.md)
   to get the connection URL.
 
 - Generate a 32-byte random key and base64-encode it. For example:
@@ -104,7 +104,7 @@ if you need to rotate keys, you can perform the following procedure:
 - Generate a new encryption key following the same procedure as above.
 
 - Add the above key to the list of
-  [external token encryption keys](../../reference/cli/server.md#--external-token-encryption-keys).
+  [external token encryption keys](../../reference/cli/server/index.md#--external-token-encryption-keys).
   **The new key must appear first in the list**. For example, in the Kubernetes
   secret created above:
 
@@ -124,13 +124,13 @@ data:
   encrypted with the old key(s).
 
 - To re-encrypt all encrypted database fields with the new key, run
-  [`coder server dbcrypt rotate`](../../reference/cli/server_dbcrypt_rotate.md).
+  [`coder server dbcrypt rotate`](../../reference/cli/server/dbcrypt/rotate.md).
   This command will re-encrypt all tokens with the specified new encryption key.
   We recommend performing this action during a maintenance window.
 
   This command requires direct access to the database.
   If you are using the built-in PostgreSQL database, you can run
-  [`coder server postgres-builtin-url`](../../reference/cli/server_postgres-builtin-url.md)
+  [`coder server postgres-builtin-url`](../../reference/cli/server/postgres-builtin-url.md)
   to get the connection URL.
 
 - Once the above command completes successfully, remove the old encryption key
@@ -149,7 +149,7 @@ To disable encryption, perform the following actions:
   being written, which may cause the next step to fail.
 
 - Run
-  [`coder server dbcrypt decrypt`](../../reference/cli/server_dbcrypt_decrypt.md).
+  [`coder server dbcrypt decrypt`](../../reference/cli/server/dbcrypt/decrypt.md).
   This command will decrypt all encrypted user tokens and revoke all active
   encryption keys.
 
@@ -160,7 +160,7 @@ To disable encryption, perform the following actions:
   > to help prevent accidentally decrypting data.
 
 - Remove all
-  [external token encryption keys](../../reference/cli/server.md#--external-token-encryption-keys)
+  [external token encryption keys](../../reference/cli/server/index.md#--external-token-encryption-keys)
   from Coder's configuration.
 
 - Start `coderd`. You can now safely delete the encryption keys from your secret
@@ -181,12 +181,12 @@ To delete all encrypted data from your database, perform the following actions:
   being written.
 
 - Run
-  [`coder server dbcrypt delete`](../../reference/cli/server_dbcrypt_delete.md).
+  [`coder server dbcrypt delete`](../../reference/cli/server/dbcrypt/delete.md).
   This command will delete all encrypted user tokens and revoke all active
   encryption keys.
 
 - Remove all
-  [external token encryption keys](../../reference/cli/server.md#--external-token-encryption-keys)
+  [external token encryption keys](../../reference/cli/server/index.md#--external-token-encryption-keys)
   from Coder's configuration.
 
 - Start `coderd`. You can now safely delete the encryption keys from your secret
diff --git a/docs/admin/setup/configuration-reference.md b/docs/admin/setup/configuration-reference.md
index d8d5c3c651..e05a5d27cb 100644
--- a/docs/admin/setup/configuration-reference.md
+++ b/docs/admin/setup/configuration-reference.md
@@ -20,7 +20,7 @@ only the methods that apply to it.
 - A key in a YAML configuration file passed with `--config`.
 
 For a full description of each option's accepted values and behavior, follow the
-flag link into the [`coder server` CLI reference](../../reference/cli/server.md).
+flag link into the [`coder server` CLI reference](../../reference/cli/server/index.md).
 
 Deprecated options are listed at the end of each section.
 
@@ -31,7 +31,7 @@ Deprecated options are listed at the end of each section.
 The directory to cache temporary files. If unspecified and $CACHE_DIRECTORY is set, it will be used for compatibility with systemd. This directory is NOT safe to be configured as a shared directory across coderd/provisionerd replicas.
 
 - Environment variable: `CODER_CACHE_DIRECTORY`
-- CLI flag: [`--cache-dir`](../../reference/cli/server.md#--cache-dir)
+- CLI flag: [`--cache-dir`](../../reference/cli/server/index.md#--cache-dir)
 - YAML key: `cacheDir`
 - Default value: `~/.cache/coder`
 
@@ -40,7 +40,7 @@ The directory to cache temporary files. If unspecified and $CACHE_DIRECTORY is s
 The default lifetime duration for OAuth2 refresh tokens. This controls how long refresh tokens remain valid after issuance or rotation.
 
 - Environment variable: `CODER_DEFAULT_OAUTH_REFRESH_LIFETIME`
-- CLI flag: [`--default-oauth-refresh-lifetime`](../../reference/cli/server.md#--default-oauth-refresh-lifetime)
+- CLI flag: [`--default-oauth-refresh-lifetime`](../../reference/cli/server/index.md#--default-oauth-refresh-lifetime)
 - YAML key: `defaultOAuthRefreshLifetime`
 - Default value: `720h0m0s`
 
@@ -49,7 +49,7 @@ The default lifetime duration for OAuth2 refresh tokens. This controls how long
 The default lifetime duration for API tokens. This value is used when creating a token without specifying a duration, such as when authenticating the CLI or an IDE plugin.
 
 - Environment variable: `CODER_DEFAULT_TOKEN_LIFETIME`
-- CLI flag: [`--default-token-lifetime`](../../reference/cli/server.md#--default-token-lifetime)
+- CLI flag: [`--default-token-lifetime`](../../reference/cli/server/index.md#--default-token-lifetime)
 - YAML key: `defaultTokenLifetime`
 - Default value: `168h0m0s`
 
@@ -58,7 +58,7 @@ The default lifetime duration for API tokens. This value is used when creating a
 Disable caller-supplied tools in chats. Chat requests that include unsafe_dynamic_tools or inline_mcp_servers are rejected, and existing chats run without their dynamic tools and inline MCP servers.
 
 - Environment variable: `CODER_DISABLE_CHAT_CALLER_SUPPLIED_TOOLS`
-- CLI flag: [`--disable-chat-caller-supplied-tools`](../../reference/cli/server.md#--disable-chat-caller-supplied-tools)
+- CLI flag: [`--disable-chat-caller-supplied-tools`](../../reference/cli/server/index.md#--disable-chat-caller-supplied-tools)
 - YAML key: `disableChatCallerSuppliedTools`
 
 ### Disable chat sharing
@@ -66,7 +66,7 @@ Disable caller-supplied tools in chats. Chat requests that include unsafe_dynami
 Disable chat sharing. Chat ACL checking is disabled and only owners can access their chats.
 
 - Environment variable: `CODER_DISABLE_CHAT_SHARING`
-- CLI flag: [`--disable-chat-sharing`](../../reference/cli/server.md#--disable-chat-sharing)
+- CLI flag: [`--disable-chat-sharing`](../../reference/cli/server/index.md#--disable-chat-sharing)
 - YAML key: `disableChatSharing`
 
 ### Disable owner workspace access
@@ -74,7 +74,7 @@ Disable chat sharing. Chat ACL checking is disabled and only owners can access t
 Remove the permission for the 'owner' role to have workspace execution on all workspaces. This prevents the 'owner' from ssh, apps, and terminal access based on the 'owner' role. They still have their user permissions to access their own workspaces.
 
 - Environment variable: `CODER_DISABLE_OWNER_WORKSPACE_ACCESS`
-- CLI flag: [`--disable-owner-workspace-access`](../../reference/cli/server.md#--disable-owner-workspace-access)
+- CLI flag: [`--disable-owner-workspace-access`](../../reference/cli/server/index.md#--disable-owner-workspace-access)
 - YAML key: `disableOwnerWorkspaceAccess`
 
 ### Disable path apps
@@ -82,7 +82,7 @@ Remove the permission for the 'owner' role to have workspace execution on all wo
 Disable workspace apps that are not served from subdomains. Path-based apps can make requests to the Coder API and pose a security risk when the workspace serves malicious JavaScript. This is recommended for security purposes if a --wildcard-access-url is configured.
 
 - Environment variable: `CODER_DISABLE_PATH_APPS`
-- CLI flag: [`--disable-path-apps`](../../reference/cli/server.md#--disable-path-apps)
+- CLI flag: [`--disable-path-apps`](../../reference/cli/server/index.md#--disable-path-apps)
 - YAML key: `disablePathApps`
 
 ### Disable user secret file path
@@ -90,7 +90,7 @@ Disable workspace apps that are not served from subdomains. Path-based apps can
 Disable Coder-managed file path delivery for user secrets. Stored paths remain until users clear them and resume if this setting is turned off.
 
 - Environment variable: `CODER_DISABLE_USER_SECRET_FILE_PATH`
-- CLI flag: [`--disable-user-secret-file-path`](../../reference/cli/server.md#--disable-user-secret-file-path)
+- CLI flag: [`--disable-user-secret-file-path`](../../reference/cli/server/index.md#--disable-user-secret-file-path)
 - YAML key: `disableUserSecretFilePath`
 
 ### Disable workspace agent context sync
@@ -98,7 +98,7 @@ Disable Coder-managed file path delivery for user secrets. Stored paths remain u
 Stop persisting workspace agent context snapshots (instructions, skills, and MCP state used for pinned chat context). When set, coderd rejects agent context pushes as unimplemented and agents stop sending them; chats cannot pin workspace context. Use this to shed the database write load of context sync on large deployments.
 
 - Environment variable: `CODER_DISABLE_WORKSPACE_AGENT_CONTEXT_SYNC`
-- CLI flag: [`--disable-workspace-agent-context-sync`](../../reference/cli/server.md#--disable-workspace-agent-context-sync)
+- CLI flag: [`--disable-workspace-agent-context-sync`](../../reference/cli/server/index.md#--disable-workspace-agent-context-sync)
 - YAML key: `disableWorkspaceAgentContextSync`
 
 ### Disable workspace sharing
@@ -106,7 +106,7 @@ Stop persisting workspace agent context snapshots (instructions, skills, and MCP
 Disable workspace sharing. Workspace ACL checking is disabled and only owners can have ssh, apps and terminal access to workspaces. Access based on the 'owner' role is also allowed unless disabled via --disable-owner-workspace-access.
 
 - Environment variable: `CODER_DISABLE_WORKSPACE_SHARING`
-- CLI flag: [`--disable-workspace-sharing`](../../reference/cli/server.md#--disable-workspace-sharing)
+- CLI flag: [`--disable-workspace-sharing`](../../reference/cli/server/index.md#--disable-workspace-sharing)
 - YAML key: `disableWorkspaceSharing`
 
 ### Enable swagger endpoint
@@ -114,7 +114,7 @@ Disable workspace sharing. Workspace ACL checking is disabled and only owners ca
 Expose the swagger endpoint via /swagger.
 
 - Environment variable: `CODER_SWAGGER_ENABLE`
-- CLI flag: [`--swagger-enable`](../../reference/cli/server.md#--swagger-enable)
+- CLI flag: [`--swagger-enable`](../../reference/cli/server/index.md#--swagger-enable)
 - YAML key: `enableSwagger`
 
 ### Experiments
@@ -122,7 +122,7 @@ Expose the swagger endpoint via /swagger.
 Enable one or more experiments. These are not ready for production. Separate multiple experiments with commas, or enter '*' to opt-in to all available experiments.
 
 - Environment variable: `CODER_EXPERIMENTS`
-- CLI flag: [`--experiments`](../../reference/cli/server.md#--experiments)
+- CLI flag: [`--experiments`](../../reference/cli/server/index.md#--experiments)
 - YAML key: `experiments`
 
 ### External auth GitHub default provider enable
@@ -130,7 +130,7 @@ Enable one or more experiments. These are not ready for production. Separate mul
 Enable the default GitHub external auth provider managed by Coder.
 
 - Environment variable: `CODER_EXTERNAL_AUTH_GITHUB_DEFAULT_PROVIDER_ENABLE`
-- CLI flag: [`--external-auth-github-default-provider-enable`](../../reference/cli/server.md#--external-auth-github-default-provider-enable)
+- CLI flag: [`--external-auth-github-default-provider-enable`](../../reference/cli/server/index.md#--external-auth-github-default-provider-enable)
 - YAML key: `externalAuthGithubDefaultProviderEnable`
 - Default value: `true`
 
@@ -139,14 +139,14 @@ Enable the default GitHub external auth provider managed by Coder.
 Encrypt OIDC and Git authentication tokens with AES-256-GCM in the database. The value must be a comma-separated list of base64-encoded keys. Each key, when base64-decoded, must be exactly 32 bytes in length. The first key will be used to encrypt new values. Subsequent keys will be used as a fallback when decrypting. During normal operation it is recommended to only set one key unless you are in the process of rotating keys with the `coder server dbcrypt rotate` command.
 
 - Environment variable: `CODER_EXTERNAL_TOKEN_ENCRYPTION_KEYS`
-- CLI flag: [`--external-token-encryption-keys`](../../reference/cli/server.md#--external-token-encryption-keys)
+- CLI flag: [`--external-token-encryption-keys`](../../reference/cli/server/index.md#--external-token-encryption-keys)
 
 ### Postgres auth
 
 Type of auth to use when connecting to postgres. For AWS RDS, using IAM authentication (awsiamrds) is recommended.
 
 - Environment variable: `CODER_PG_AUTH`
-- CLI flag: [`--postgres-auth`](../../reference/cli/server.md#--postgres-auth)
+- CLI flag: [`--postgres-auth`](../../reference/cli/server/index.md#--postgres-auth)
 - YAML key: `pgAuth`
 - Default value: `password`
 
@@ -155,7 +155,7 @@ Type of auth to use when connecting to postgres. For AWS RDS, using IAM authenti
 Maximum number of idle connections to the database. Set to "auto" (the default) to use max open / 3. Value must be greater or equal to 0; 0 means explicitly no idle connections.
 
 - Environment variable: `CODER_PG_CONN_MAX_IDLE`
-- CLI flag: [`--postgres-conn-max-idle`](../../reference/cli/server.md#--postgres-conn-max-idle)
+- CLI flag: [`--postgres-conn-max-idle`](../../reference/cli/server/index.md#--postgres-conn-max-idle)
 - YAML key: `pgConnMaxIdle`
 - Default value: `auto`
 
@@ -164,7 +164,7 @@ Maximum number of idle connections to the database. Set to "auto" (the default)
 Maximum number of open connections to the database. Defaults to 10.
 
 - Environment variable: `CODER_PG_CONN_MAX_OPEN`
-- CLI flag: [`--postgres-conn-max-open`](../../reference/cli/server.md#--postgres-conn-max-open)
+- CLI flag: [`--postgres-conn-max-open`](../../reference/cli/server/index.md#--postgres-conn-max-open)
 - YAML key: `pgConnMaxOpen`
 - Default value: `10`
 
@@ -173,21 +173,21 @@ Maximum number of open connections to the database. Defaults to 10.
 URL of a PostgreSQL database. If empty, PostgreSQL binaries will be downloaded from Maven (https://repo1.maven.org/maven2) and store all data in the config root. Access the built-in database with "coder server postgres-builtin-url". Note that any special characters in the URL must be URL-encoded.
 
 - Environment variable: `CODER_PG_CONNECTION_URL`
-- CLI flag: [`--postgres-url`](../../reference/cli/server.md#--postgres-url)
+- CLI flag: [`--postgres-url`](../../reference/cli/server/index.md#--postgres-url)
 
 ### SCIM API key
 
 Enables SCIM and sets the authentication header for the built-in SCIM server. New users are automatically created with OIDC authentication.
 
 - Environment variable: `CODER_SCIM_AUTH_HEADER`
-- CLI flag: [`--scim-auth-header`](../../reference/cli/server.md#--scim-auth-header)
+- CLI flag: [`--scim-auth-header`](../../reference/cli/server/index.md#--scim-auth-header)
 
 ### SCIM use legacy
 
 Use the legacy SCIM implementation instead of the SCIM 2.0 handler. This is provided for backward compatibility for existing users.
 
 - Environment variable: `CODER_SCIM_USE_LEGACY`
-- CLI flag: [`--scim-use-legacy`](../../reference/cli/server.md#--scim-use-legacy)
+- CLI flag: [`--scim-use-legacy`](../../reference/cli/server/index.md#--scim-use-legacy)
 - YAML key: `scimUseLegacy`
 - Default value: `true`
 
@@ -196,7 +196,7 @@ Use the legacy SCIM implementation instead of the SCIM 2.0 handler. This is prov
 The algorithm to use for generating ssh keys. Accepted values are "ed25519", "ecdsa", or "rsa4096".
 
 - Environment variable: `CODER_SSH_KEYGEN_ALGORITHM`
-- CLI flag: [`--ssh-keygen-algorithm`](../../reference/cli/server.md#--ssh-keygen-algorithm)
+- CLI flag: [`--ssh-keygen-algorithm`](../../reference/cli/server/index.md#--ssh-keygen-algorithm)
 - YAML key: `sshKeygenAlgorithm`
 - Default value: `ed25519`
 
@@ -205,7 +205,7 @@ The algorithm to use for generating ssh keys. Accepted values are "ed25519", "ec
 Support links to display in the top right drop down menu.
 
 - Environment variable: `CODER_SUPPORT_LINKS`
-- CLI flag: [`--support-links`](../../reference/cli/server.md#--support-links)
+- CLI flag: [`--support-links`](../../reference/cli/server/index.md#--support-links)
 - YAML key: `supportLinks`
 
 ### Terms of service URL
@@ -213,7 +213,7 @@ Support links to display in the top right drop down menu.
 A URL to an external Terms of Service that must be accepted by users when logging in.
 
 - Environment variable: `CODER_TERMS_OF_SERVICE_URL`
-- CLI flag: [`--terms-of-service-url`](../../reference/cli/server.md#--terms-of-service-url)
+- CLI flag: [`--terms-of-service-url`](../../reference/cli/server/index.md#--terms-of-service-url)
 - YAML key: `termsOfServiceURL`
 
 ### Update check
@@ -221,7 +221,7 @@ A URL to an external Terms of Service that must be accepted by users when loggin
 Periodically check for new releases of Coder and inform the owner. The check is performed once per day.
 
 - Environment variable: `CODER_UPDATE_CHECK`
-- CLI flag: [`--update-check`](../../reference/cli/server.md#--update-check)
+- CLI flag: [`--update-check`](../../reference/cli/server/index.md#--update-check)
 - YAML key: `updateCheck`
 - Default value: `false`
 
@@ -232,7 +232,7 @@ Periodically check for new releases of Coder and inform the owner. The check is
 Determines when accumulated AI spend resets to zero, aligned to UTC calendar boundaries. Only "month" is currently supported.
 
 - Environment variable: `CODER_AI_BUDGET_PERIOD`
-- CLI flag: [`--ai-budget-period`](../../reference/cli/server.md#--ai-budget-period)
+- CLI flag: [`--ai-budget-period`](../../reference/cli/server/index.md#--ai-budget-period)
 - YAML key: `ai_gateway.budget_period`
 - Default value: `month`
 
@@ -241,7 +241,7 @@ Determines when accumulated AI spend resets to zero, aligned to UTC calendar bou
 Determines the effective group when a user belongs to multiple groups with AI budgets. "highest" selects the group with the largest spend limit, and is currently the only supported value.
 
 - Environment variable: `CODER_AI_BUDGET_POLICY`
-- CLI flag: [`--ai-budget-policy`](../../reference/cli/server.md#--ai-budget-policy)
+- CLI flag: [`--ai-budget-policy`](../../reference/cli/server/index.md#--ai-budget-policy)
 - YAML key: `ai_gateway.budget_policy`
 - Default value: `highest`
 
@@ -250,7 +250,7 @@ Determines the effective group when a user belongs to multiple groups with AI bu
 Base directory for dumping AI Gateway request/response pairs to disk for debugging. When set, each provider writes under a subdirectory named after the provider. Sensitive headers are redacted. Leave empty to disable.
 
 - Environment variable: `CODER_AI_GATEWAY_DUMP_DIR`
-- CLI flag: [`--ai-gateway-dump-dir`](../../reference/cli/server.md#--ai-gateway-dump-dir)
+- CLI flag: [`--ai-gateway-dump-dir`](../../reference/cli/server/index.md#--ai-gateway-dump-dir)
 - YAML key: `ai_gateway.api_dump_dir`
 
 ### Allow BYOK
@@ -258,7 +258,7 @@ Base directory for dumping AI Gateway request/response pairs to disk for debuggi
 Allow users to provide their own LLM API keys or subscriptions. When disabled, only centralized key authentication is permitted.
 
 - Environment variable: `CODER_AI_GATEWAY_ALLOW_BYOK`
-- CLI flag: [`--ai-gateway-allow-byok`](../../reference/cli/server.md#--ai-gateway-allow-byok)
+- CLI flag: [`--ai-gateway-allow-byok`](../../reference/cli/server/index.md#--ai-gateway-allow-byok)
 - YAML key: `ai_gateway.allow_byok`
 - Default value: `true`
 
@@ -267,7 +267,7 @@ Allow users to provide their own LLM API keys or subscriptions. When disabled, o
 Enable the circuit breaker to protect against cascading failures from upstream AI provider overload (503, 529).
 
 - Environment variable: `CODER_AI_GATEWAY_CIRCUIT_BREAKER_ENABLED`
-- CLI flag: [`--ai-gateway-circuit-breaker-enabled`](../../reference/cli/server.md#--ai-gateway-circuit-breaker-enabled)
+- CLI flag: [`--ai-gateway-circuit-breaker-enabled`](../../reference/cli/server/index.md#--ai-gateway-circuit-breaker-enabled)
 - YAML key: `ai_gateway.circuit_breaker_enabled`
 - Default value: `false`
 
@@ -276,7 +276,7 @@ Enable the circuit breaker to protect against cascading failures from upstream A
 Length of time to retain data such as interceptions and all related records (token, prompt, tool use).
 
 - Environment variable: `CODER_AI_GATEWAY_RETENTION`
-- CLI flag: [`--ai-gateway-retention`](../../reference/cli/server.md#--ai-gateway-retention)
+- CLI flag: [`--ai-gateway-retention`](../../reference/cli/server/index.md#--ai-gateway-retention)
 - YAML key: `ai_gateway.retention`
 - Default value: `60d`
 
@@ -285,7 +285,7 @@ Length of time to retain data such as interceptions and all related records (tok
 Whether to start an in-memory AI Gateway instance.
 
 - Environment variable: `CODER_AI_GATEWAY_ENABLED`
-- CLI flag: [`--ai-gateway-enabled`](../../reference/cli/server.md#--ai-gateway-enabled)
+- CLI flag: [`--ai-gateway-enabled`](../../reference/cli/server/index.md#--ai-gateway-enabled)
 - YAML key: `ai_gateway.enabled`
 - Default value: `true`
 
@@ -294,7 +294,7 @@ Whether to start an in-memory AI Gateway instance.
 Maximum number of concurrent AI Gateway requests per replica. Set to 0 to disable (unlimited).
 
 - Environment variable: `CODER_AI_GATEWAY_MAX_CONCURRENCY`
-- CLI flag: [`--ai-gateway-max-concurrency`](../../reference/cli/server.md#--ai-gateway-max-concurrency)
+- CLI flag: [`--ai-gateway-max-concurrency`](../../reference/cli/server/index.md#--ai-gateway-max-concurrency)
 - YAML key: `ai_gateway.max_concurrency`
 - Default value: `0`
 
@@ -303,7 +303,7 @@ Maximum number of concurrent AI Gateway requests per replica. Set to 0 to disabl
 Maximum number of AI Gateway requests per second per replica. Set to 0 to disable (unlimited).
 
 - Environment variable: `CODER_AI_GATEWAY_RATE_LIMIT`
-- CLI flag: [`--ai-gateway-rate-limit`](../../reference/cli/server.md#--ai-gateway-rate-limit)
+- CLI flag: [`--ai-gateway-rate-limit`](../../reference/cli/server/index.md#--ai-gateway-rate-limit)
 - YAML key: `ai_gateway.rate_limit`
 - Default value: `0`
 
@@ -312,7 +312,7 @@ Maximum number of AI Gateway requests per second per replica. Set to 0 to disabl
 Once enabled, extra headers will be added to upstream requests to identify the user (actor) making requests to AI Gateway. This is only needed if you are using a proxy between AI Gateway and an upstream AI provider. This will send X-Ai-Bridge-Actor-Id (the ID of the user making the request) and X-Ai-Bridge-Actor-Metadata-Username (their username).
 
 - Environment variable: `CODER_AI_GATEWAY_SEND_ACTOR_HEADERS`
-- CLI flag: [`--ai-gateway-send-actor-headers`](../../reference/cli/server.md#--ai-gateway-send-actor-headers)
+- CLI flag: [`--ai-gateway-send-actor-headers`](../../reference/cli/server/index.md#--ai-gateway-send-actor-headers)
 - YAML key: `ai_gateway.send_actor_headers`
 - Default value: `false`
 
@@ -321,7 +321,7 @@ Once enabled, extra headers will be added to upstream requests to identify the u
 Emit structured logs for AI Gateway interception records. Use this for exporting these records to external SIEM or observability systems.
 
 - Environment variable: `CODER_AI_GATEWAY_STRUCTURED_LOGGING`
-- CLI flag: [`--ai-gateway-structured-logging`](../../reference/cli/server.md#--ai-gateway-structured-logging)
+- CLI flag: [`--ai-gateway-structured-logging`](../../reference/cli/server/index.md#--ai-gateway-structured-logging)
 - YAML key: `ai_gateway.structured_logging`
 - Default value: `false`
 
@@ -332,7 +332,7 @@ Emit structured logs for AI Gateway interception records. Use this for exporting
 Directory for dumping MITM request/response pairs to disk for debugging. When set, each proxied request produces .req.txt and .resp.txt files organized by provider. Sensitive headers are redacted. Leave empty to disable.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_DUMP_DIR`
-- CLI flag: [`--ai-gateway-proxy-dump-dir`](../../reference/cli/server.md#--ai-gateway-proxy-dump-dir)
+- CLI flag: [`--ai-gateway-proxy-dump-dir`](../../reference/cli/server/index.md#--ai-gateway-proxy-dump-dir)
 - YAML key: `ai_gateway_proxy.api_dump_dir`
 
 ### Allowed private CIDRs
@@ -340,7 +340,7 @@ Directory for dumping MITM request/response pairs to disk for debugging. When se
 Comma-separated list of CIDR ranges that are permitted even though they fall within blocked private/reserved IP ranges. By default all private ranges are blocked to prevent SSRF attacks. Use this to allow access to specific internal networks.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_ALLOWED_PRIVATE_CIDRS`
-- CLI flag: [`--ai-gateway-proxy-allowed-private-cidrs`](../../reference/cli/server.md#--ai-gateway-proxy-allowed-private-cidrs)
+- CLI flag: [`--ai-gateway-proxy-allowed-private-cidrs`](../../reference/cli/server/index.md#--ai-gateway-proxy-allowed-private-cidrs)
 - YAML key: `ai_gateway_proxy.allowed_private_cidrs`
 
 ### Enabled
@@ -348,7 +348,7 @@ Comma-separated list of CIDR ranges that are permitted even though they fall wit
 Enable the AI Gateway MITM Proxy for intercepting and decrypting AI provider requests.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_ENABLED`
-- CLI flag: [`--ai-gateway-proxy-enabled`](../../reference/cli/server.md#--ai-gateway-proxy-enabled)
+- CLI flag: [`--ai-gateway-proxy-enabled`](../../reference/cli/server/index.md#--ai-gateway-proxy-enabled)
 - YAML key: `ai_gateway_proxy.enabled`
 - Default value: `false`
 
@@ -357,7 +357,7 @@ Enable the AI Gateway MITM Proxy for intercepting and decrypting AI provider req
 The address the AI Gateway Proxy will listen on.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_LISTEN_ADDR`
-- CLI flag: [`--ai-gateway-proxy-listen-addr`](../../reference/cli/server.md#--ai-gateway-proxy-listen-addr)
+- CLI flag: [`--ai-gateway-proxy-listen-addr`](../../reference/cli/server/index.md#--ai-gateway-proxy-listen-addr)
 - YAML key: `ai_gateway_proxy.listen_addr`
 - Default value: `:8888`
 
@@ -366,7 +366,7 @@ The address the AI Gateway Proxy will listen on.
 Path to the CA certificate file used to intercept (MITM) HTTPS traffic from AI clients. This CA must be trusted by AI clients for the proxy to decrypt their requests.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_CERT_FILE`
-- CLI flag: [`--ai-gateway-proxy-cert-file`](../../reference/cli/server.md#--ai-gateway-proxy-cert-file)
+- CLI flag: [`--ai-gateway-proxy-cert-file`](../../reference/cli/server/index.md#--ai-gateway-proxy-cert-file)
 - YAML key: `ai_gateway_proxy.cert_file`
 
 ### MITM CA key file
@@ -374,7 +374,7 @@ Path to the CA certificate file used to intercept (MITM) HTTPS traffic from AI c
 Path to the CA private key file used to intercept (MITM) HTTPS traffic from AI clients.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_KEY_FILE`
-- CLI flag: [`--ai-gateway-proxy-key-file`](../../reference/cli/server.md#--ai-gateway-proxy-key-file)
+- CLI flag: [`--ai-gateway-proxy-key-file`](../../reference/cli/server/index.md#--ai-gateway-proxy-key-file)
 - YAML key: `ai_gateway_proxy.key_file`
 
 ### TLS certificate file
@@ -382,7 +382,7 @@ Path to the CA private key file used to intercept (MITM) HTTPS traffic from AI c
 Path to the TLS certificate file for the AI Gateway Proxy listener. Must be set together with AI Gateway Proxy TLS Key File.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_TLS_CERT_FILE`
-- CLI flag: [`--ai-gateway-proxy-tls-cert-file`](../../reference/cli/server.md#--ai-gateway-proxy-tls-cert-file)
+- CLI flag: [`--ai-gateway-proxy-tls-cert-file`](../../reference/cli/server/index.md#--ai-gateway-proxy-tls-cert-file)
 - YAML key: `ai_gateway_proxy.tls_cert_file`
 
 ### TLS key file
@@ -390,7 +390,7 @@ Path to the TLS certificate file for the AI Gateway Proxy listener. Must be set
 Path to the TLS private key file for the AI Gateway Proxy listener. Must be set together with AI Gateway Proxy TLS Certificate File.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_TLS_KEY_FILE`
-- CLI flag: [`--ai-gateway-proxy-tls-key-file`](../../reference/cli/server.md#--ai-gateway-proxy-tls-key-file)
+- CLI flag: [`--ai-gateway-proxy-tls-key-file`](../../reference/cli/server/index.md#--ai-gateway-proxy-tls-key-file)
 - YAML key: `ai_gateway_proxy.tls_key_file`
 
 ### Target
@@ -398,7 +398,7 @@ Path to the TLS private key file for the AI Gateway Proxy listener. Must be set
 Base URL of the AI Gateway to forward intercepted requests to. Defaults to the embedded AI Gateway address at the Coder access URL plus /api/v2/ai-gateway.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_TARGET`
-- CLI flag: [`--ai-gateway-proxy-target`](../../reference/cli/server.md#--ai-gateway-proxy-target)
+- CLI flag: [`--ai-gateway-proxy-target`](../../reference/cli/server/index.md#--ai-gateway-proxy-target)
 - YAML key: `ai_gateway_proxy.target`
 
 ### Upstream proxy
@@ -406,7 +406,7 @@ Base URL of the AI Gateway to forward intercepted requests to. Defaults to the e
 URL of an upstream HTTP proxy to chain tunneled (non-allowlisted) requests through. Format: http://[user:pass@]host:port or https://[user:pass@]host:port.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_UPSTREAM`
-- CLI flag: [`--ai-gateway-proxy-upstream`](../../reference/cli/server.md#--ai-gateway-proxy-upstream)
+- CLI flag: [`--ai-gateway-proxy-upstream`](../../reference/cli/server/index.md#--ai-gateway-proxy-upstream)
 - YAML key: `ai_gateway_proxy.upstream_proxy`
 
 ### Upstream proxy CA
@@ -414,7 +414,7 @@ URL of an upstream HTTP proxy to chain tunneled (non-allowlisted) requests throu
 Path to a PEM-encoded CA certificate to trust for the upstream proxy's TLS connection. Only needed for HTTPS upstream proxies with certificates not trusted by the system. If not provided, the system certificate pool is used.
 
 - Environment variable: `CODER_AI_GATEWAY_PROXY_UPSTREAM_CA`
-- CLI flag: [`--ai-gateway-proxy-upstream-ca`](../../reference/cli/server.md#--ai-gateway-proxy-upstream-ca)
+- CLI flag: [`--ai-gateway-proxy-upstream-ca`](../../reference/cli/server/index.md#--ai-gateway-proxy-upstream-ca)
 - YAML key: `ai_gateway_proxy.upstream_proxy_ca`
 
 ## Chat
@@ -426,7 +426,7 @@ Configure the background chat processing daemon.
 Force chat debug logging on for every chat, bypassing the runtime admin and user opt-in settings.
 
 - Environment variable: `CODER_CHAT_DEBUG_LOGGING_ENABLED`
-- CLI flag: [`--chat-debug-logging-enabled`](../../reference/cli/server.md#--chat-debug-logging-enabled)
+- CLI flag: [`--chat-debug-logging-enabled`](../../reference/cli/server/index.md#--chat-debug-logging-enabled)
 - YAML key: `chat.debugLoggingEnabled`
 - Default value: `false`
 
@@ -435,7 +435,7 @@ Force chat debug logging on for every chat, bypassing the runtime admin and user
 Maximum number of files linked to a chat, including user uploads, files the agent attaches, and desktop recordings and their thumbnails. Linking a file beyond the limit permanently deletes the chat's earliest-uploaded files, and earlier messages show them as expired. A message that includes more files than the limit is rejected with HTTP 400. Must be at least 1.
 
 - Environment variable: `CODER_CHAT_MAX_ATTACHMENTS_PER_CHAT`
-- CLI flag: [`--chat-max-attachments-per-chat`](../../reference/cli/server.md#--chat-max-attachments-per-chat)
+- CLI flag: [`--chat-max-attachments-per-chat`](../../reference/cli/server/index.md#--chat-max-attachments-per-chat)
 - YAML key: `chat.maxAttachmentsPerChat`
 - Default value: `50`
 
@@ -444,7 +444,7 @@ Maximum number of files linked to a chat, including user uploads, files the agen
 Maximum number of virtual desktop recordings that each Coder server stores at the same time. Each upload holds the recording and its thumbnail in memory, up to 110 MB. Additional recordings wait for a free slot and are discarded if none frees up within 90 seconds. Must be at least 1.
 
 - Environment variable: `CODER_CHAT_MAX_CONCURRENT_RECORDING_UPLOADS`
-- CLI flag: [`--chat-max-concurrent-recording-uploads`](../../reference/cli/server.md#--chat-max-concurrent-recording-uploads)
+- CLI flag: [`--chat-max-concurrent-recording-uploads`](../../reference/cli/server/index.md#--chat-max-concurrent-recording-uploads)
 - YAML key: `chat.maxConcurrentRecordingUploads`
 - Default value: `25`
 
@@ -453,7 +453,7 @@ Maximum number of virtual desktop recordings that each Coder server stores at th
 Maximum number of consecutive retries after a model generation fails with a transient error, such as a rate limit, an overloaded provider, or a stream that stops sending data. The count resets after each successful step. When the retries run out, the chat moves to the error state and shows the provider error. Advisor calls and the generation of chat titles, summaries, and turn status labels use the same limit. Must be at least 1.
 
 - Environment variable: `CODER_CHAT_MAX_GENERATION_RETRIES`
-- CLI flag: [`--chat-max-generation-retries`](../../reference/cli/server.md#--chat-max-generation-retries)
+- CLI flag: [`--chat-max-generation-retries`](../../reference/cli/server/index.md#--chat-max-generation-retries)
 - YAML key: `chat.maxGenerationRetries`
 - Default value: `25`
 
@@ -462,7 +462,7 @@ Maximum number of consecutive retries after a model generation fails with a tran
 Maximum size in bytes of the deployment system prompt, the plan mode instructions, and each user's custom prompt. Saving a longer prompt fails with HTTP 400. Lowering the limit does not affect prompts that are already saved. Must be at least 1.
 
 - Environment variable: `CODER_CHAT_MAX_PROMPT_BYTES`
-- CLI flag: [`--chat-max-prompt-bytes`](../../reference/cli/server.md#--chat-max-prompt-bytes)
+- CLI flag: [`--chat-max-prompt-bytes`](../../reference/cli/server/index.md#--chat-max-prompt-bytes)
 - YAML key: `chat.maxPromptBytes`
 - Default value: `131072`
 
@@ -471,7 +471,7 @@ Maximum size in bytes of the deployment system prompt, the plan mode instruction
 Maximum number of messages that can be queued in a chat. Sending a message to a chat whose queue is full fails with HTTP 429. Must be at least 1.
 
 - Environment variable: `CODER_CHAT_MAX_QUEUED_MESSAGES_PER_CHAT`
-- CLI flag: [`--chat-max-queued-messages-per-chat`](../../reference/cli/server.md#--chat-max-queued-messages-per-chat)
+- CLI flag: [`--chat-max-queued-messages-per-chat`](../../reference/cli/server/index.md#--chat-max-queued-messages-per-chat)
 - YAML key: `chat.maxQueuedMessagesPerChat`
 - Default value: `20`
 
@@ -480,7 +480,7 @@ Maximum number of messages that can be queued in a chat. Sending a message to a
 Maximum number of steps in a chat turn. Each model response is one step; compaction summaries, advisor calls, and retried attempts do not count. A turn that reaches the limit runs the tools from the last response, then ends without an error. Must be at least 1.
 
 - Environment variable: `CODER_CHAT_MAX_STEPS_PER_TURN`
-- CLI flag: [`--chat-max-steps-per-turn`](../../reference/cli/server.md#--chat-max-steps-per-turn)
+- CLI flag: [`--chat-max-steps-per-turn`](../../reference/cli/server/index.md#--chat-max-steps-per-turn)
 - YAML key: `chat.maxStepsPerTurn`
 - Default value: `1200`
 
@@ -489,7 +489,7 @@ Maximum number of steps in a chat turn. Each model response is one step; compact
 Maximum time to wait for the next streamed part from the chat model before the attempt is canceled and retried. This also bounds the time to first token. Set to 0 to disable. Must be no more than 24h.
 
 - Environment variable: `CODER_CHAT_STREAM_SILENCE_TIMEOUT`
-- CLI flag: [`--chat-stream-silence-timeout`](../../reference/cli/server.md#--chat-stream-silence-timeout)
+- CLI flag: [`--chat-stream-silence-timeout`](../../reference/cli/server/index.md#--chat-stream-silence-timeout)
 - YAML key: `chat.streamSilenceTimeout`
 - Default value: `10m0s`
 
@@ -502,7 +502,7 @@ These options change the behavior of how clients interact with the Coder. Client
 The upgrade message to display to users when a client/server mismatch is detected. By default it instructs users to update using 'curl -fsSL https://coder.com/install.sh | sh'.
 
 - Environment variable: `CODER_CLI_UPGRADE_MESSAGE`
-- CLI flag: [`--cli-upgrade-message`](../../reference/cli/server.md#--cli-upgrade-message)
+- CLI flag: [`--cli-upgrade-message`](../../reference/cli/server/index.md#--cli-upgrade-message)
 - YAML key: `client.cliUpgradeMessage`
 
 ### SSH config options
@@ -510,7 +510,7 @@ The upgrade message to display to users when a client/server mismatch is detecte
 These SSH config options will override the default SSH config options. Provide options in "key=value" or "key value" format separated by commas. Using this incorrectly can break SSH to your deployment, use cautiously. The following options are not allowed: Host, Match, Include, ProxyCommand, ProxyJump, LocalCommand, PermitLocalCommand, RemoteCommand, KnownHostsCommand, PKCS11Provider, SecurityKeyProvider, SmartcardDevice, XAuthLocation. Option values must not contain newline, carriage return, or NUL characters.
 
 - Environment variable: `CODER_SSH_CONFIG_OPTIONS`
-- CLI flag: [`--ssh-config-options`](../../reference/cli/server.md#--ssh-config-options)
+- CLI flag: [`--ssh-config-options`](../../reference/cli/server/index.md#--ssh-config-options)
 - YAML key: `client.sshConfigOptions`
 
 ### Web terminal renderer
@@ -518,7 +518,7 @@ These SSH config options will override the default SSH config options. Provide o
 The renderer to use when opening a web terminal. Valid values are 'canvas', 'webgl', or 'dom'.
 
 - Environment variable: `CODER_WEB_TERMINAL_RENDERER`
-- CLI flag: [`--web-terminal-renderer`](../../reference/cli/server.md#--web-terminal-renderer)
+- CLI flag: [`--web-terminal-renderer`](../../reference/cli/server/index.md#--web-terminal-renderer)
 - YAML key: `client.webTerminalRenderer`
 - Default value: `canvas`
 
@@ -527,7 +527,7 @@ The renderer to use when opening a web terminal. Valid values are 'canvas', 'web
 Workspace hostnames use this suffix in SSH config and Coder Connect on Coder Desktop. By default it is coder, resulting in names like myworkspace.coder. The suffix must not start with a dot, and must not contain spaces, newlines, or glob characters (* and ?).
 
 - Environment variable: `CODER_WORKSPACE_HOSTNAME_SUFFIX`
-- CLI flag: [`--workspace-hostname-suffix`](../../reference/cli/server.md#--workspace-hostname-suffix)
+- CLI flag: [`--workspace-hostname-suffix`](../../reference/cli/server/index.md#--workspace-hostname-suffix)
 - YAML key: `client.workspaceHostnameSuffix`
 - Default value: `coder`
 
@@ -540,13 +540,13 @@ Use a YAML configuration file when your server launch become unwieldy.
 Specify a YAML file to load configuration from.
 
 - Environment variable: `CODER_CONFIG_PATH`
-- CLI flag: [`--config`](../../reference/cli/server.md#-c---config)
+- CLI flag: [`--config`](../../reference/cli/server/index.md#-c---config)
 
 ### Write config
 
 Write out the current server config as YAML to stdout.
 
-- CLI flag: [`--write-config`](../../reference/cli/server.md#--write-config)
+- CLI flag: [`--write-config`](../../reference/cli/server/index.md#--write-config)
 
 ## Email
 
@@ -557,7 +557,7 @@ Configure how emails are sent.
 Force a TLS connection to the configured SMTP smarthost.
 
 - Environment variable: `CODER_EMAIL_FORCE_TLS`
-- CLI flag: [`--email-force-tls`](../../reference/cli/server.md#--email-force-tls)
+- CLI flag: [`--email-force-tls`](../../reference/cli/server/index.md#--email-force-tls)
 - YAML key: `email.forceTLS`
 - Default value: `false`
 
@@ -566,7 +566,7 @@ Force a TLS connection to the configured SMTP smarthost.
 The sender's address to use.
 
 - Environment variable: `CODER_EMAIL_FROM`
-- CLI flag: [`--email-from`](../../reference/cli/server.md#--email-from)
+- CLI flag: [`--email-from`](../../reference/cli/server/index.md#--email-from)
 - YAML key: `email.from`
 
 ### Hello
@@ -574,7 +574,7 @@ The sender's address to use.
 The hostname identifying the SMTP server.
 
 - Environment variable: `CODER_EMAIL_HELLO`
-- CLI flag: [`--email-hello`](../../reference/cli/server.md#--email-hello)
+- CLI flag: [`--email-hello`](../../reference/cli/server/index.md#--email-hello)
 - YAML key: `email.hello`
 - Default value: `localhost`
 
@@ -583,7 +583,7 @@ The hostname identifying the SMTP server.
 The intermediary SMTP host through which emails are sent.
 
 - Environment variable: `CODER_EMAIL_SMARTHOST`
-- CLI flag: [`--email-smarthost`](../../reference/cli/server.md#--email-smarthost)
+- CLI flag: [`--email-smarthost`](../../reference/cli/server/index.md#--email-smarthost)
 - YAML key: `email.smarthost`
 
 ### Email authentication
@@ -595,7 +595,7 @@ Configure SMTP authentication options.
 Identity to use with PLAIN authentication.
 
 - Environment variable: `CODER_EMAIL_AUTH_IDENTITY`
-- CLI flag: [`--email-auth-identity`](../../reference/cli/server.md#--email-auth-identity)
+- CLI flag: [`--email-auth-identity`](../../reference/cli/server/index.md#--email-auth-identity)
 - YAML key: `email.emailAuth.identity`
 
 #### Password
@@ -603,14 +603,14 @@ Identity to use with PLAIN authentication.
 Password to use with PLAIN/LOGIN authentication.
 
 - Environment variable: `CODER_EMAIL_AUTH_PASSWORD`
-- CLI flag: [`--email-auth-password`](../../reference/cli/server.md#--email-auth-password)
+- CLI flag: [`--email-auth-password`](../../reference/cli/server/index.md#--email-auth-password)
 
 #### Password file
 
 File from which to load password for use with PLAIN/LOGIN authentication.
 
 - Environment variable: `CODER_EMAIL_AUTH_PASSWORD_FILE`
-- CLI flag: [`--email-auth-password-file`](../../reference/cli/server.md#--email-auth-password-file)
+- CLI flag: [`--email-auth-password-file`](../../reference/cli/server/index.md#--email-auth-password-file)
 - YAML key: `email.emailAuth.passwordFile`
 
 #### Username
@@ -618,7 +618,7 @@ File from which to load password for use with PLAIN/LOGIN authentication.
 Username to use with PLAIN/LOGIN authentication.
 
 - Environment variable: `CODER_EMAIL_AUTH_USERNAME`
-- CLI flag: [`--email-auth-username`](../../reference/cli/server.md#--email-auth-username)
+- CLI flag: [`--email-auth-username`](../../reference/cli/server/index.md#--email-auth-username)
 - YAML key: `email.emailAuth.username`
 
 ### Email TLS
@@ -630,7 +630,7 @@ Configure TLS for your SMTP server target.
 CA certificate file to use.
 
 - Environment variable: `CODER_EMAIL_TLS_CACERTFILE`
-- CLI flag: [`--email-tls-ca-cert-file`](../../reference/cli/server.md#--email-tls-ca-cert-file)
+- CLI flag: [`--email-tls-ca-cert-file`](../../reference/cli/server/index.md#--email-tls-ca-cert-file)
 - YAML key: `email.emailTLS.caCertFile`
 
 #### Certificate file
@@ -638,7 +638,7 @@ CA certificate file to use.
 Certificate file to use.
 
 - Environment variable: `CODER_EMAIL_TLS_CERTFILE`
-- CLI flag: [`--email-tls-cert-file`](../../reference/cli/server.md#--email-tls-cert-file)
+- CLI flag: [`--email-tls-cert-file`](../../reference/cli/server/index.md#--email-tls-cert-file)
 - YAML key: `email.emailTLS.certFile`
 
 #### Certificate key file
@@ -646,7 +646,7 @@ Certificate file to use.
 Certificate key file to use.
 
 - Environment variable: `CODER_EMAIL_TLS_CERTKEYFILE`
-- CLI flag: [`--email-tls-cert-key-file`](../../reference/cli/server.md#--email-tls-cert-key-file)
+- CLI flag: [`--email-tls-cert-key-file`](../../reference/cli/server/index.md#--email-tls-cert-key-file)
 - YAML key: `email.emailTLS.certKeyFile`
 
 #### Server name
@@ -654,7 +654,7 @@ Certificate key file to use.
 Server name to verify against the target certificate.
 
 - Environment variable: `CODER_EMAIL_TLS_SERVERNAME`
-- CLI flag: [`--email-tls-server-name`](../../reference/cli/server.md#--email-tls-server-name)
+- CLI flag: [`--email-tls-server-name`](../../reference/cli/server/index.md#--email-tls-server-name)
 - YAML key: `email.emailTLS.serverName`
 
 #### Skip certificate verification (insecure)
@@ -662,7 +662,7 @@ Server name to verify against the target certificate.
 Skip verification of the target server's certificate (insecure).
 
 - Environment variable: `CODER_EMAIL_TLS_SKIPVERIFY`
-- CLI flag: [`--email-tls-skip-verify`](../../reference/cli/server.md#--email-tls-skip-verify)
+- CLI flag: [`--email-tls-skip-verify`](../../reference/cli/server/index.md#--email-tls-skip-verify)
 - YAML key: `email.emailTLS.insecureSkipVerify`
 
 #### StartTLS
@@ -670,7 +670,7 @@ Skip verification of the target server's certificate (insecure).
 Enable STARTTLS to upgrade insecure SMTP connections using TLS.
 
 - Environment variable: `CODER_EMAIL_TLS_STARTTLS`
-- CLI flag: [`--email-tls-starttls`](../../reference/cli/server.md#--email-tls-starttls)
+- CLI flag: [`--email-tls-starttls`](../../reference/cli/server/index.md#--email-tls-starttls)
 - YAML key: `email.emailTLS.startTLS`
 
 ## Introspection
@@ -684,7 +684,7 @@ Configure logging, tracing, stat collection, and metrics exporting.
 Refresh interval for healthchecks.
 
 - Environment variable: `CODER_HEALTH_CHECK_REFRESH`
-- CLI flag: [`--health-check-refresh`](../../reference/cli/server.md#--health-check-refresh)
+- CLI flag: [`--health-check-refresh`](../../reference/cli/server/index.md#--health-check-refresh)
 - YAML key: `introspection.healthcheck.refresh`
 - Default value: `10m0s`
 
@@ -693,7 +693,7 @@ Refresh interval for healthchecks.
 The threshold for the database health check. If the median latency of the database exceeds this threshold over 5 attempts, the database is considered unhealthy. The default value is 15ms.
 
 - Environment variable: `CODER_HEALTH_CHECK_THRESHOLD_DATABASE`
-- CLI flag: [`--health-check-threshold-database`](../../reference/cli/server.md#--health-check-threshold-database)
+- CLI flag: [`--health-check-threshold-database`](../../reference/cli/server/index.md#--health-check-threshold-database)
 - YAML key: `introspection.healthcheck.thresholdDatabase`
 - Default value: `15ms`
 
@@ -704,7 +704,7 @@ The threshold for the database health check. If the median latency of the databa
 Allow administrators to enable Terraform debug output.
 
 - Environment variable: `CODER_ENABLE_TERRAFORM_DEBUG_MODE`
-- CLI flag: [`--enable-terraform-debug-mode`](../../reference/cli/server.md#--enable-terraform-debug-mode)
+- CLI flag: [`--enable-terraform-debug-mode`](../../reference/cli/server/index.md#--enable-terraform-debug-mode)
 - YAML key: `introspection.logging.enableTerraformDebugMode`
 - Default value: `false`
 
@@ -713,7 +713,7 @@ Allow administrators to enable Terraform debug output.
 Output human-readable logs to a given file.
 
 - Environment variable: `CODER_LOGGING_HUMAN`
-- CLI flag: [`--log-human`](../../reference/cli/server.md#--log-human)
+- CLI flag: [`--log-human`](../../reference/cli/server/index.md#--log-human)
 - YAML key: `introspection.logging.humanPath`
 - Default value: `/dev/stderr`
 
@@ -722,7 +722,7 @@ Output human-readable logs to a given file.
 Output JSON logs to a given file.
 
 - Environment variable: `CODER_LOGGING_JSON`
-- CLI flag: [`--log-json`](../../reference/cli/server.md#--log-json)
+- CLI flag: [`--log-json`](../../reference/cli/server/index.md#--log-json)
 - YAML key: `introspection.logging.jsonPath`
 
 #### Log filter
@@ -730,7 +730,7 @@ Output JSON logs to a given file.
 Filter debug logs by matching against a given regex. Use .* to match all debug logs.
 
 - Environment variable: `CODER_LOG_FILTER`
-- CLI flag: [`--log-filter`](../../reference/cli/server.md#-l---log-filter)
+- CLI flag: [`--log-filter`](../../reference/cli/server/index.md#-l---log-filter)
 - YAML key: `introspection.logging.filter`
 
 #### Stackdriver log location
@@ -738,7 +738,7 @@ Filter debug logs by matching against a given regex. Use .* to match all debug l
 Output Stackdriver compatible logs to a given file.
 
 - Environment variable: `CODER_LOGGING_STACKDRIVER`
-- CLI flag: [`--log-stackdriver`](../../reference/cli/server.md#--log-stackdriver)
+- CLI flag: [`--log-stackdriver`](../../reference/cli/server/index.md#--log-stackdriver)
 - YAML key: `introspection.logging.stackdriverPath`
 
 ### Prometheus
@@ -748,7 +748,7 @@ Output Stackdriver compatible logs to a given file.
 The bind address to serve prometheus metrics.
 
 - Environment variable: `CODER_PROMETHEUS_ADDRESS`
-- CLI flag: [`--prometheus-address`](../../reference/cli/server.md#--prometheus-address)
+- CLI flag: [`--prometheus-address`](../../reference/cli/server/index.md#--prometheus-address)
 - YAML key: `introspection.prometheus.address`
 - Default value: `127.0.0.1:2112`
 
@@ -757,7 +757,7 @@ The bind address to serve prometheus metrics.
 When collecting agent stats, aggregate metrics by a given set of comma-separated labels to reduce cardinality. Accepted values are agent_name, template_name, username, workspace_name.
 
 - Environment variable: `CODER_PROMETHEUS_AGGREGATE_AGENT_STATS_BY`
-- CLI flag: [`--prometheus-aggregate-agent-stats-by`](../../reference/cli/server.md#--prometheus-aggregate-agent-stats-by)
+- CLI flag: [`--prometheus-aggregate-agent-stats-by`](../../reference/cli/server/index.md#--prometheus-aggregate-agent-stats-by)
 - YAML key: `introspection.prometheus.aggregate_agent_stats_by`
 - Default value: `agent_name,template_name,username,workspace_name`
 
@@ -766,7 +766,7 @@ When collecting agent stats, aggregate metrics by a given set of comma-separated
 Collect agent stats (may increase charges for metrics storage).
 
 - Environment variable: `CODER_PROMETHEUS_COLLECT_AGENT_STATS`
-- CLI flag: [`--prometheus-collect-agent-stats`](../../reference/cli/server.md#--prometheus-collect-agent-stats)
+- CLI flag: [`--prometheus-collect-agent-stats`](../../reference/cli/server/index.md#--prometheus-collect-agent-stats)
 - YAML key: `introspection.prometheus.collect_agent_stats`
 
 #### Collect database metrics
@@ -774,7 +774,7 @@ Collect agent stats (may increase charges for metrics storage).
 Collect database query metrics (may increase charges for metrics storage). If set to false, a reduced set of database metrics are still collected.
 
 - Environment variable: `CODER_PROMETHEUS_COLLECT_DB_METRICS`
-- CLI flag: [`--prometheus-collect-db-metrics`](../../reference/cli/server.md#--prometheus-collect-db-metrics)
+- CLI flag: [`--prometheus-collect-db-metrics`](../../reference/cli/server/index.md#--prometheus-collect-db-metrics)
 - YAML key: `introspection.prometheus.collect_db_metrics`
 - Default value: `false`
 
@@ -783,7 +783,7 @@ Collect database query metrics (may increase charges for metrics storage). If se
 Serve prometheus metrics on the address defined by prometheus address.
 
 - Environment variable: `CODER_PROMETHEUS_ENABLE`
-- CLI flag: [`--prometheus-enable`](../../reference/cli/server.md#--prometheus-enable)
+- CLI flag: [`--prometheus-enable`](../../reference/cli/server/index.md#--prometheus-enable)
 - YAML key: `introspection.prometheus.enable`
 
 ### Stats collection
@@ -795,7 +795,7 @@ Serve prometheus metrics on the address defined by prometheus address.
 Enable the collection of application and workspace usage along with the associated API endpoints and the template insights page. Disabling this will also disable traffic and connection insights in the deployment stats shown to admins in the bottom bar of the Coder UI, and will prevent Prometheus collection of these values.
 
 - Environment variable: `CODER_STATS_COLLECTION_USAGE_STATS_ENABLE`
-- CLI flag: [`--stats-collection-usage-stats-enable`](../../reference/cli/server.md#--stats-collection-usage-stats-enable)
+- CLI flag: [`--stats-collection-usage-stats-enable`](../../reference/cli/server/index.md#--stats-collection-usage-stats-enable)
 - YAML key: `introspection.statsCollection.usageStats.enable`
 - Default value: `true`
 
@@ -806,7 +806,7 @@ Enable the collection of application and workspace usage along with the associat
 Enables capturing of logs as events in traces. This is useful for debugging, but may result in a very large amount of events being sent to the tracing backend which may incur significant costs.
 
 - Environment variable: `CODER_TRACE_LOGS`
-- CLI flag: [`--trace-logs`](../../reference/cli/server.md#--trace-logs)
+- CLI flag: [`--trace-logs`](../../reference/cli/server/index.md#--trace-logs)
 - YAML key: `introspection.tracing.captureLogs`
 
 #### Trace enable
@@ -814,7 +814,7 @@ Enables capturing of logs as events in traces. This is useful for debugging, but
 Whether application tracing data is collected. It exports to a backend configured by environment variables. See: https://github.com/open-telemetry/opentelemetry-specification/blob/main/specification/protocol/exporter.md.
 
 - Environment variable: `CODER_TRACE_ENABLE`
-- CLI flag: [`--trace`](../../reference/cli/server.md#--trace)
+- CLI flag: [`--trace`](../../reference/cli/server/index.md#--trace)
 - YAML key: `introspection.tracing.enable`
 
 #### Trace Honeycomb API key
@@ -822,7 +822,7 @@ Whether application tracing data is collected. It exports to a backend configure
 Enables trace exporting to Honeycomb.io using the provided API Key.
 
 - Environment variable: `CODER_TRACE_HONEYCOMB_API_KEY`
-- CLI flag: [`--trace-honeycomb-api-key`](../../reference/cli/server.md#--trace-honeycomb-api-key)
+- CLI flag: [`--trace-honeycomb-api-key`](../../reference/cli/server/index.md#--trace-honeycomb-api-key)
 
 ### pprof
 
@@ -831,7 +831,7 @@ Enables trace exporting to Honeycomb.io using the provided API Key.
 The bind address to serve pprof.
 
 - Environment variable: `CODER_PPROF_ADDRESS`
-- CLI flag: [`--pprof-address`](../../reference/cli/server.md#--pprof-address)
+- CLI flag: [`--pprof-address`](../../reference/cli/server/index.md#--pprof-address)
 - YAML key: `introspection.pprof.address`
 - Default value: `127.0.0.1:6060`
 
@@ -840,7 +840,7 @@ The bind address to serve pprof.
 Serve pprof metrics on the address defined by pprof address.
 
 - Environment variable: `CODER_PPROF_ENABLE`
-- CLI flag: [`--pprof-enable`](../../reference/cli/server.md#--pprof-enable)
+- CLI flag: [`--pprof-enable`](../../reference/cli/server/index.md#--pprof-enable)
 - YAML key: `introspection.pprof.enable`
 
 ## MCP
@@ -850,7 +850,7 @@ Serve pprof metrics on the address defined by pprof address.
 MCP server destinations in private or reserved IP ranges are blocked by default for SSRF protection. This applies to OAuth2 discovery, OAuth2 token and revocation exchanges, and runtime MCP connections from coderd. This option exempts specific CIDRs.
 
 - Environment variable: `CODER_MCP_ALLOWED_PRIVATE_CIDRS`
-- CLI flag: [`--mcp-allowed-private-cidrs`](../../reference/cli/server.md#--mcp-allowed-private-cidrs)
+- CLI flag: [`--mcp-allowed-private-cidrs`](../../reference/cli/server/index.md#--mcp-allowed-private-cidrs)
 - YAML key: `mcp.allowed_private_cidrs`
 
 ## Networking
@@ -860,7 +860,7 @@ MCP server destinations in private or reserved IP ranges are blocked by default
 The URL that users will use to access the Coder deployment.
 
 - Environment variable: `CODER_ACCESS_URL`
-- CLI flag: [`--access-url`](../../reference/cli/server.md#--access-url)
+- CLI flag: [`--access-url`](../../reference/cli/server/index.md#--access-url)
 - YAML key: `networking.accessURL`
 
 ### Browser only
@@ -868,7 +868,7 @@ The URL that users will use to access the Coder deployment.
 Whether Coder only allows connections to workspaces via the browser.
 
 - Environment variable: `CODER_BROWSER_ONLY`
-- CLI flag: [`--browser-only`](../../reference/cli/server.md#--browser-only)
+- CLI flag: [`--browser-only`](../../reference/cli/server/index.md#--browser-only)
 - YAML key: `networking.browserOnly`
 
 ### Docs URL
@@ -876,7 +876,7 @@ Whether Coder only allows connections to workspaces via the browser.
 Specifies the custom docs URL.
 
 - Environment variable: `CODER_DOCS_URL`
-- CLI flag: [`--docs-url`](../../reference/cli/server.md#--docs-url)
+- CLI flag: [`--docs-url`](../../reference/cli/server/index.md#--docs-url)
 - YAML key: `networking.docsURL`
 - Default value: `https://coder.com/docs`
 
@@ -885,7 +885,7 @@ Specifies the custom docs URL.
 Headers to trust for forwarding IP addresses. e.g. Cf-Connecting-Ip, True-Client-Ip, X-Forwarded-For.
 
 - Environment variable: `CODER_PROXY_TRUSTED_HEADERS`
-- CLI flag: [`--proxy-trusted-headers`](../../reference/cli/server.md#--proxy-trusted-headers)
+- CLI flag: [`--proxy-trusted-headers`](../../reference/cli/server/index.md#--proxy-trusted-headers)
 - YAML key: `networking.proxyTrustedHeaders`
 
 ### Proxy trusted origins
@@ -893,7 +893,7 @@ Headers to trust for forwarding IP addresses. e.g. Cf-Connecting-Ip, True-Client
 Origin addresses to respect "proxy-trusted-headers" and X-Forwarded-Host for subdomain app routing. e.g. 192.168.1.0/24.
 
 - Environment variable: `CODER_PROXY_TRUSTED_ORIGINS`
-- CLI flag: [`--proxy-trusted-origins`](../../reference/cli/server.md#--proxy-trusted-origins)
+- CLI flag: [`--proxy-trusted-origins`](../../reference/cli/server/index.md#--proxy-trusted-origins)
 - YAML key: `networking.proxyTrustedOrigins`
 
 ### Redirect to access URL
@@ -901,7 +901,7 @@ Origin addresses to respect "proxy-trusted-headers" and X-Forwarded-Host for sub
 Specifies whether to redirect requests that do not match the access URL host.
 
 - Environment variable: `CODER_REDIRECT_TO_ACCESS_URL`
-- CLI flag: [`--redirect-to-access-url`](../../reference/cli/server.md#--redirect-to-access-url)
+- CLI flag: [`--redirect-to-access-url`](../../reference/cli/server/index.md#--redirect-to-access-url)
 - YAML key: `networking.redirectToAccessURL`
 
 ### SameSite auth cookie
@@ -909,7 +909,7 @@ Specifies whether to redirect requests that do not match the access URL host.
 Controls the 'SameSite' property is set on browser session cookies.
 
 - Environment variable: `CODER_SAMESITE_AUTH_COOKIE`
-- CLI flag: [`--samesite-auth-cookie`](../../reference/cli/server.md#--samesite-auth-cookie)
+- CLI flag: [`--samesite-auth-cookie`](../../reference/cli/server/index.md#--samesite-auth-cookie)
 - YAML key: `networking.sameSiteAuthCookie`
 - Default value: `lax`
 
@@ -918,7 +918,7 @@ Controls the 'SameSite' property is set on browser session cookies.
 Controls if the 'Secure' property is set on browser session cookies.
 
 - Environment variable: `CODER_SECURE_AUTH_COOKIE`
-- CLI flag: [`--secure-auth-cookie`](../../reference/cli/server.md#--secure-auth-cookie)
+- CLI flag: [`--secure-auth-cookie`](../../reference/cli/server/index.md#--secure-auth-cookie)
 - YAML key: `networking.secureAuthCookie`
 - Default value: `(computed at runtime)`
 
@@ -927,7 +927,7 @@ Controls if the 'Secure' property is set on browser session cookies.
 Specifies the wildcard hostname to use for workspace applications in the form "*.example.com".
 
 - Environment variable: `CODER_WILDCARD_ACCESS_URL`
-- CLI flag: [`--wildcard-access-url`](../../reference/cli/server.md#--wildcard-access-url)
+- CLI flag: [`--wildcard-access-url`](../../reference/cli/server/index.md#--wildcard-access-url)
 - YAML key: `networking.wildcardAccessURL`
 
 ### __Host prefix cookies
@@ -935,7 +935,7 @@ Specifies the wildcard hostname to use for workspace applications in the form "*
 Recommended to be enabled. Enables `__Host-` prefix for cookies to guarantee they are only set by the right domain. This change is disruptive to any workspaces built before release 2.31, requiring a workspace restart.
 
 - Environment variable: `CODER_HOST_PREFIX_COOKIE`
-- CLI flag: [`--host-prefix-cookie`](../../reference/cli/server.md#--host-prefix-cookie)
+- CLI flag: [`--host-prefix-cookie`](../../reference/cli/server/index.md#--host-prefix-cookie)
 - YAML key: `networking.hostPrefixCookie`
 - Default value: `false`
 
@@ -948,7 +948,7 @@ Configure network clustering. Coder Servers in the primary region form a cluster
 Hostname or (more commonly) IP to reach this replica for clustering.
 
 - Environment variable: `CODER_CLUSTER_HOST`
-- CLI flag: [`--cluster-host`](../../reference/cli/server.md#--cluster-host)
+- CLI flag: [`--cluster-host`](../../reference/cli/server/index.md#--cluster-host)
 - YAML key: `networking.cluster.clusterHost`
 
 ### DERP
@@ -960,7 +960,7 @@ Most Coder deployments never have to think about DERP because all connections be
 Block peer-to-peer (aka. direct) workspace connections. All workspace connections from the CLI will be proxied through Coder (or custom configured DERP servers) and will never be peer-to-peer when enabled. Workspaces may still reach out to STUN servers to get their address until they are restarted after this change has been made, but new connections will still be proxied regardless.
 
 - Environment variable: `CODER_BLOCK_DIRECT`
-- CLI flag: [`--block-direct-connections`](../../reference/cli/server.md#--block-direct-connections)
+- CLI flag: [`--block-direct-connections`](../../reference/cli/server/index.md#--block-direct-connections)
 - YAML key: `networking.derp.blockDirect`
 
 #### Config path
@@ -968,7 +968,7 @@ Block peer-to-peer (aka. direct) workspace connections. All workspace connection
 Path to read a DERP mapping from. See: https://tailscale.com/kb/1118/custom-derp-servers/.
 
 - Environment variable: `CODER_DERP_CONFIG_PATH`
-- CLI flag: [`--derp-config-path`](../../reference/cli/server.md#--derp-config-path)
+- CLI flag: [`--derp-config-path`](../../reference/cli/server/index.md#--derp-config-path)
 - YAML key: `networking.derp.configPath`
 
 #### Config URL
@@ -976,7 +976,7 @@ Path to read a DERP mapping from. See: https://tailscale.com/kb/1118/custom-derp
 URL to fetch a DERP mapping on startup. See: https://tailscale.com/kb/1118/custom-derp-servers/.
 
 - Environment variable: `CODER_DERP_CONFIG_URL`
-- CLI flag: [`--derp-config-url`](../../reference/cli/server.md#--derp-config-url)
+- CLI flag: [`--derp-config-url`](../../reference/cli/server/index.md#--derp-config-url)
 - YAML key: `networking.derp.url`
 
 #### Force WebSockets
@@ -984,7 +984,7 @@ URL to fetch a DERP mapping on startup. See: https://tailscale.com/kb/1118/custo
 Force clients and agents to always use WebSocket to connect to DERP relay servers. By default, DERP uses `Upgrade: derp`, which may cause issues with some reverse proxies. Clients may automatically fallback to WebSocket if they detect an issue with `Upgrade: derp`, but this does not work in all situations.
 
 - Environment variable: `CODER_DERP_FORCE_WEBSOCKETS`
-- CLI flag: [`--derp-force-websockets`](../../reference/cli/server.md#--derp-force-websockets)
+- CLI flag: [`--derp-force-websockets`](../../reference/cli/server/index.md#--derp-force-websockets)
 - YAML key: `networking.derp.forceWebSockets`
 
 #### Server enable
@@ -992,7 +992,7 @@ Force clients and agents to always use WebSocket to connect to DERP relay server
 Whether to enable or disable the embedded DERP relay server.
 
 - Environment variable: `CODER_DERP_SERVER_ENABLE`
-- CLI flag: [`--derp-server-enable`](../../reference/cli/server.md#--derp-server-enable)
+- CLI flag: [`--derp-server-enable`](../../reference/cli/server/index.md#--derp-server-enable)
 - YAML key: `networking.derp.enable`
 - Default value: `true`
 
@@ -1001,7 +1001,7 @@ Whether to enable or disable the embedded DERP relay server.
 Region name that for the embedded DERP server.
 
 - Environment variable: `CODER_DERP_SERVER_REGION_NAME`
-- CLI flag: [`--derp-server-region-name`](../../reference/cli/server.md#--derp-server-region-name)
+- CLI flag: [`--derp-server-region-name`](../../reference/cli/server/index.md#--derp-server-region-name)
 - YAML key: `networking.derp.regionName`
 - Default value: `Coder Embedded Relay`
 
@@ -1010,7 +1010,7 @@ Region name that for the embedded DERP server.
 An HTTP URL that is accessible by other replicas to relay DERP traffic. Required for high availability.
 
 - Environment variable: `CODER_DERP_SERVER_RELAY_URL`
-- CLI flag: [`--derp-server-relay-url`](../../reference/cli/server.md#--derp-server-relay-url)
+- CLI flag: [`--derp-server-relay-url`](../../reference/cli/server/index.md#--derp-server-relay-url)
 - YAML key: `networking.derp.relayURL`
 
 #### Server STUN addresses
@@ -1018,7 +1018,7 @@ An HTTP URL that is accessible by other replicas to relay DERP traffic. Required
 Addresses for STUN servers to establish P2P connections. It's recommended to have at least two STUN servers to give users the best chance of connecting P2P to workspaces. Each STUN server will get it's own DERP region, with region IDs starting at `--derp-server-region-id + 1`. Use special value 'disable' to turn off STUN completely.
 
 - Environment variable: `CODER_DERP_SERVER_STUN_ADDRESSES`
-- CLI flag: [`--derp-server-stun-addresses`](../../reference/cli/server.md#--derp-server-stun-addresses)
+- CLI flag: [`--derp-server-stun-addresses`](../../reference/cli/server/index.md#--derp-server-stun-addresses)
 - YAML key: `networking.derp.stunAddresses`
 - Default value: `stun.l.google.com:19302,stun1.l.google.com:19302,stun2.l.google.com:19302,stun3.l.google.com:19302,stun4.l.google.com:19302`
 
@@ -1029,7 +1029,7 @@ Addresses for STUN servers to establish P2P connections. It's recommended to hav
 Coder configures a Content Security Policy (CSP) to protect against XSS attacks. This setting allows you to add additional CSP directives, which can open the attack surface of the deployment. Format matches the CSP directive format, e.g. --additional-csp-policy="script-src https://example.com".
 
 - Environment variable: `CODER_ADDITIONAL_CSP_POLICY`
-- CLI flag: [`--additional-csp-policy`](../../reference/cli/server.md#--additional-csp-policy)
+- CLI flag: [`--additional-csp-policy`](../../reference/cli/server/index.md#--additional-csp-policy)
 - YAML key: `networking.http.additionalCSPPolicy`
 
 #### Disable password authentication
@@ -1037,7 +1037,7 @@ Coder configures a Content Security Policy (CSP) to protect against XSS attacks.
 Disable password authentication. This is recommended for security purposes in production deployments that rely on an identity provider. Any user with the owner role will be able to sign in with their password regardless of this setting to avoid potential lock out. If you are locked out of your account, you can use the `coder server create-admin` command to create a new admin user directly in the database.
 
 - Environment variable: `CODER_DISABLE_PASSWORD_AUTH`
-- CLI flag: [`--disable-password-auth`](../../reference/cli/server.md#--disable-password-auth)
+- CLI flag: [`--disable-password-auth`](../../reference/cli/server/index.md#--disable-password-auth)
 - YAML key: `networking.http.disablePasswordAuth`
 
 #### Disable session expiry refresh
@@ -1045,7 +1045,7 @@ Disable password authentication. This is recommended for security purposes in pr
 Disable automatic session expiry bumping due to activity. This forces all sessions to become invalid after the session expiry duration has been reached.
 
 - Environment variable: `CODER_DISABLE_SESSION_EXPIRY_REFRESH`
-- CLI flag: [`--disable-session-expiry-refresh`](../../reference/cli/server.md#--disable-session-expiry-refresh)
+- CLI flag: [`--disable-session-expiry-refresh`](../../reference/cli/server/index.md#--disable-session-expiry-refresh)
 - YAML key: `networking.http.disableSessionExpiryRefresh`
 
 #### Address
@@ -1053,7 +1053,7 @@ Disable automatic session expiry bumping due to activity. This forces all sessio
 HTTP bind address of the server. Unset to disable the HTTP endpoint.
 
 - Environment variable: `CODER_HTTP_ADDRESS`
-- CLI flag: [`--http-address`](../../reference/cli/server.md#--http-address)
+- CLI flag: [`--http-address`](../../reference/cli/server/index.md#--http-address)
 - YAML key: `networking.http.httpAddress`
 - Default value: `127.0.0.1:3000`
 
@@ -1062,7 +1062,7 @@ HTTP bind address of the server. Unset to disable the HTTP endpoint.
 The maximum lifetime duration users can specify when creating an API token.
 
 - Environment variable: `CODER_MAX_TOKEN_LIFETIME`
-- CLI flag: [`--max-token-lifetime`](../../reference/cli/server.md#--max-token-lifetime)
+- CLI flag: [`--max-token-lifetime`](../../reference/cli/server/index.md#--max-token-lifetime)
 - YAML key: `networking.http.maxTokenLifetime`
 - Default value: `876600h0m0s`
 
@@ -1071,7 +1071,7 @@ The maximum lifetime duration users can specify when creating an API token.
 The maximum lifetime duration administrators can specify when creating an API token.
 
 - Environment variable: `CODER_MAX_ADMIN_TOKEN_LIFETIME`
-- CLI flag: [`--max-admin-token-lifetime`](../../reference/cli/server.md#--max-admin-token-lifetime)
+- CLI flag: [`--max-admin-token-lifetime`](../../reference/cli/server/index.md#--max-admin-token-lifetime)
 - YAML key: `networking.http.maxAdminTokenLifetime`
 - Default value: `168h0m0s`
 
@@ -1080,7 +1080,7 @@ The maximum lifetime duration administrators can specify when creating an API to
 The interval in which coderd should be checking the status of workspace proxies.
 
 - Environment variable: `CODER_PROXY_HEALTH_INTERVAL`
-- CLI flag: [`--proxy-health-interval`](../../reference/cli/server.md#--proxy-health-interval)
+- CLI flag: [`--proxy-health-interval`](../../reference/cli/server/index.md#--proxy-health-interval)
 - YAML key: `networking.http.proxyHealthInterval`
 - Default value: `1m0s`
 
@@ -1089,7 +1089,7 @@ The interval in which coderd should be checking the status of workspace proxies.
 The token expiry duration for browser sessions. Sessions may last longer if they are actively making requests, but this functionality can be disabled via --disable-session-expiry-refresh.
 
 - Environment variable: `CODER_SESSION_DURATION`
-- CLI flag: [`--session-duration`](../../reference/cli/server.md#--session-duration)
+- CLI flag: [`--session-duration`](../../reference/cli/server/index.md#--session-duration)
 - YAML key: `networking.http.sessionDuration`
 - Default value: `24h0m0s`
 
@@ -1102,7 +1102,7 @@ Configure TLS / HTTPS for your Coder deployment. If you're running Coder behind
 Controls if the 'Strict-Transport-Security' header is set on all static file responses. This header should only be set if the server is accessed via HTTPS. This value is the MaxAge in seconds of the header.
 
 - Environment variable: `CODER_STRICT_TRANSPORT_SECURITY`
-- CLI flag: [`--strict-transport-security`](../../reference/cli/server.md#--strict-transport-security)
+- CLI flag: [`--strict-transport-security`](../../reference/cli/server/index.md#--strict-transport-security)
 - YAML key: `networking.tls.strictTransportSecurity`
 - Default value: `0`
 
@@ -1111,7 +1111,7 @@ Controls if the 'Strict-Transport-Security' header is set on all static file res
 Two optional fields can be set in the Strict-Transport-Security header; 'includeSubDomains' and 'preload'. The 'strict-transport-security' flag must be set to a non-zero value for these options to be used.
 
 - Environment variable: `CODER_STRICT_TRANSPORT_SECURITY_OPTIONS`
-- CLI flag: [`--strict-transport-security-options`](../../reference/cli/server.md#--strict-transport-security-options)
+- CLI flag: [`--strict-transport-security-options`](../../reference/cli/server/index.md#--strict-transport-security-options)
 - YAML key: `networking.tls.strictTransportSecurityOptions`
 
 #### Address
@@ -1119,7 +1119,7 @@ Two optional fields can be set in the Strict-Transport-Security header; 'include
 HTTPS bind address of the server.
 
 - Environment variable: `CODER_TLS_ADDRESS`
-- CLI flag: [`--tls-address`](../../reference/cli/server.md#--tls-address)
+- CLI flag: [`--tls-address`](../../reference/cli/server/index.md#--tls-address)
 - YAML key: `networking.tls.address`
 - Default value: `127.0.0.1:3443`
 
@@ -1128,7 +1128,7 @@ HTTPS bind address of the server.
 By default, only ciphers marked as 'secure' are allowed to be used. See https://github.com/golang/go/blob/master/src/crypto/tls/cipher_suites.go#L82-L95.
 
 - Environment variable: `CODER_TLS_ALLOW_INSECURE_CIPHERS`
-- CLI flag: [`--tls-allow-insecure-ciphers`](../../reference/cli/server.md#--tls-allow-insecure-ciphers)
+- CLI flag: [`--tls-allow-insecure-ciphers`](../../reference/cli/server/index.md#--tls-allow-insecure-ciphers)
 - YAML key: `networking.tls.tlsAllowInsecureCiphers`
 - Default value: `false`
 
@@ -1137,7 +1137,7 @@ By default, only ciphers marked as 'secure' are allowed to be used. See https://
 Path to each certificate for TLS. It requires a PEM-encoded file. To configure the listener to use a CA certificate, concatenate the primary certificate and the CA certificate together. The primary certificate should appear first in the combined file.
 
 - Environment variable: `CODER_TLS_CERT_FILE`
-- CLI flag: [`--tls-cert-file`](../../reference/cli/server.md#--tls-cert-file)
+- CLI flag: [`--tls-cert-file`](../../reference/cli/server/index.md#--tls-cert-file)
 - YAML key: `networking.tls.certFiles`
 
 #### Ciphers
@@ -1145,7 +1145,7 @@ Path to each certificate for TLS. It requires a PEM-encoded file. To configure t
 Specify specific TLS ciphers that allowed to be used. See https://github.com/golang/go/blob/master/src/crypto/tls/cipher_suites.go#L53-L75.
 
 - Environment variable: `CODER_TLS_CIPHERS`
-- CLI flag: [`--tls-ciphers`](../../reference/cli/server.md#--tls-ciphers)
+- CLI flag: [`--tls-ciphers`](../../reference/cli/server/index.md#--tls-ciphers)
 - YAML key: `networking.tls.tlsCiphers`
 
 #### Client auth
@@ -1153,7 +1153,7 @@ Specify specific TLS ciphers that allowed to be used. See https://github.com/gol
 Policy the server will follow for TLS Client Authentication. Accepted values are "none", "request", "require-any", "verify-if-given", or "require-and-verify".
 
 - Environment variable: `CODER_TLS_CLIENT_AUTH`
-- CLI flag: [`--tls-client-auth`](../../reference/cli/server.md#--tls-client-auth)
+- CLI flag: [`--tls-client-auth`](../../reference/cli/server/index.md#--tls-client-auth)
 - YAML key: `networking.tls.clientAuth`
 - Default value: `none`
 
@@ -1162,7 +1162,7 @@ Policy the server will follow for TLS Client Authentication. Accepted values are
 PEM-encoded Certificate Authority file used for checking the authenticity of client.
 
 - Environment variable: `CODER_TLS_CLIENT_CA_FILE`
-- CLI flag: [`--tls-client-ca-file`](../../reference/cli/server.md#--tls-client-ca-file)
+- CLI flag: [`--tls-client-ca-file`](../../reference/cli/server/index.md#--tls-client-ca-file)
 - YAML key: `networking.tls.clientCAFile`
 
 #### Client cert file
@@ -1170,7 +1170,7 @@ PEM-encoded Certificate Authority file used for checking the authenticity of cli
 Path to certificate for client TLS authentication. It requires a PEM-encoded file.
 
 - Environment variable: `CODER_TLS_CLIENT_CERT_FILE`
-- CLI flag: [`--tls-client-cert-file`](../../reference/cli/server.md#--tls-client-cert-file)
+- CLI flag: [`--tls-client-cert-file`](../../reference/cli/server/index.md#--tls-client-cert-file)
 - YAML key: `networking.tls.clientCertFile`
 
 #### Client key file
@@ -1178,7 +1178,7 @@ Path to certificate for client TLS authentication. It requires a PEM-encoded fil
 Path to key for client TLS authentication. It requires a PEM-encoded file.
 
 - Environment variable: `CODER_TLS_CLIENT_KEY_FILE`
-- CLI flag: [`--tls-client-key-file`](../../reference/cli/server.md#--tls-client-key-file)
+- CLI flag: [`--tls-client-key-file`](../../reference/cli/server/index.md#--tls-client-key-file)
 - YAML key: `networking.tls.clientKeyFile`
 
 #### Enable
@@ -1186,7 +1186,7 @@ Path to key for client TLS authentication. It requires a PEM-encoded file.
 Whether TLS will be enabled.
 
 - Environment variable: `CODER_TLS_ENABLE`
-- CLI flag: [`--tls-enable`](../../reference/cli/server.md#--tls-enable)
+- CLI flag: [`--tls-enable`](../../reference/cli/server/index.md#--tls-enable)
 - YAML key: `networking.tls.enable`
 
 #### Key files
@@ -1194,7 +1194,7 @@ Whether TLS will be enabled.
 Paths to the private keys for each of the certificates. It requires a PEM-encoded file.
 
 - Environment variable: `CODER_TLS_KEY_FILE`
-- CLI flag: [`--tls-key-file`](../../reference/cli/server.md#--tls-key-file)
+- CLI flag: [`--tls-key-file`](../../reference/cli/server/index.md#--tls-key-file)
 - YAML key: `networking.tls.keyFiles`
 
 #### Minimum version
@@ -1202,7 +1202,7 @@ Paths to the private keys for each of the certificates. It requires a PEM-encode
 Minimum supported version of TLS. Accepted values are "tls10", "tls11", "tls12" or "tls13".
 
 - Environment variable: `CODER_TLS_MIN_VERSION`
-- CLI flag: [`--tls-min-version`](../../reference/cli/server.md#--tls-min-version)
+- CLI flag: [`--tls-min-version`](../../reference/cli/server/index.md#--tls-min-version)
 - YAML key: `networking.tls.minVersion`
 - Default value: `tls12`
 
@@ -1215,7 +1215,7 @@ Configure how notifications are processed and delivered.
 How long to wait while a notification is being sent before giving up.
 
 - Environment variable: `CODER_NOTIFICATIONS_DISPATCH_TIMEOUT`
-- CLI flag: [`--notifications-dispatch-timeout`](../../reference/cli/server.md#--notifications-dispatch-timeout)
+- CLI flag: [`--notifications-dispatch-timeout`](../../reference/cli/server/index.md#--notifications-dispatch-timeout)
 - YAML key: `notifications.dispatchTimeout`
 - Default value: `1m0s`
 
@@ -1224,7 +1224,7 @@ How long to wait while a notification is being sent before giving up.
 The upper limit of attempts to send a notification.
 
 - Environment variable: `CODER_NOTIFICATIONS_MAX_SEND_ATTEMPTS`
-- CLI flag: [`--notifications-max-send-attempts`](../../reference/cli/server.md#--notifications-max-send-attempts)
+- CLI flag: [`--notifications-max-send-attempts`](../../reference/cli/server/index.md#--notifications-max-send-attempts)
 - YAML key: `notifications.maxSendAttempts`
 - Default value: `5`
 
@@ -1233,7 +1233,7 @@ The upper limit of attempts to send a notification.
 Which delivery method to use (available options: 'smtp', 'webhook').
 
 - Environment variable: `CODER_NOTIFICATIONS_METHOD`
-- CLI flag: [`--notifications-method`](../../reference/cli/server.md#--notifications-method)
+- CLI flag: [`--notifications-method`](../../reference/cli/server/index.md#--notifications-method)
 - YAML key: `notifications.method`
 - Default value: `smtp`
 
@@ -1246,7 +1246,7 @@ Configure how email notifications are sent.
 **Deprecated.** Force a TLS connection to the configured SMTP smarthost.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_FORCE_TLS`
-- CLI flag: [`--notifications-email-force-tls`](../../reference/cli/server.md#--notifications-email-force-tls)
+- CLI flag: [`--notifications-email-force-tls`](../../reference/cli/server/index.md#--notifications-email-force-tls)
 - YAML key: `notifications.email.forceTLS`
 
 #### From address
@@ -1254,7 +1254,7 @@ Configure how email notifications are sent.
 **Deprecated.** The sender's address to use.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_FROM`
-- CLI flag: [`--notifications-email-from`](../../reference/cli/server.md#--notifications-email-from)
+- CLI flag: [`--notifications-email-from`](../../reference/cli/server/index.md#--notifications-email-from)
 - YAML key: `notifications.email.from`
 
 #### Hello
@@ -1262,7 +1262,7 @@ Configure how email notifications are sent.
 **Deprecated.** The hostname identifying the SMTP server.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_HELLO`
-- CLI flag: [`--notifications-email-hello`](../../reference/cli/server.md#--notifications-email-hello)
+- CLI flag: [`--notifications-email-hello`](../../reference/cli/server/index.md#--notifications-email-hello)
 - YAML key: `notifications.email.hello`
 
 #### Smarthost
@@ -1270,7 +1270,7 @@ Configure how email notifications are sent.
 **Deprecated.** The intermediary SMTP host through which emails are sent.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_SMARTHOST`
-- CLI flag: [`--notifications-email-smarthost`](../../reference/cli/server.md#--notifications-email-smarthost)
+- CLI flag: [`--notifications-email-smarthost`](../../reference/cli/server/index.md#--notifications-email-smarthost)
 - YAML key: `notifications.email.smarthost`
 
 #### Email authentication
@@ -1282,7 +1282,7 @@ Configure SMTP authentication options.
 **Deprecated.** Identity to use with PLAIN authentication.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_AUTH_IDENTITY`
-- CLI flag: [`--notifications-email-auth-identity`](../../reference/cli/server.md#--notifications-email-auth-identity)
+- CLI flag: [`--notifications-email-auth-identity`](../../reference/cli/server/index.md#--notifications-email-auth-identity)
 - YAML key: `notifications.email.emailAuth.identity`
 
 ##### Password
@@ -1290,14 +1290,14 @@ Configure SMTP authentication options.
 **Deprecated.** Password to use with PLAIN/LOGIN authentication.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_AUTH_PASSWORD`
-- CLI flag: [`--notifications-email-auth-password`](../../reference/cli/server.md#--notifications-email-auth-password)
+- CLI flag: [`--notifications-email-auth-password`](../../reference/cli/server/index.md#--notifications-email-auth-password)
 
 ##### Password file
 
 **Deprecated.** File from which to load password for use with PLAIN/LOGIN authentication.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_AUTH_PASSWORD_FILE`
-- CLI flag: [`--notifications-email-auth-password-file`](../../reference/cli/server.md#--notifications-email-auth-password-file)
+- CLI flag: [`--notifications-email-auth-password-file`](../../reference/cli/server/index.md#--notifications-email-auth-password-file)
 - YAML key: `notifications.email.emailAuth.passwordFile`
 
 ##### Username
@@ -1305,7 +1305,7 @@ Configure SMTP authentication options.
 **Deprecated.** Username to use with PLAIN/LOGIN authentication.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_AUTH_USERNAME`
-- CLI flag: [`--notifications-email-auth-username`](../../reference/cli/server.md#--notifications-email-auth-username)
+- CLI flag: [`--notifications-email-auth-username`](../../reference/cli/server/index.md#--notifications-email-auth-username)
 - YAML key: `notifications.email.emailAuth.username`
 
 #### Email TLS
@@ -1317,7 +1317,7 @@ Configure TLS for your SMTP server target.
 **Deprecated.** CA certificate file to use.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_TLS_CACERTFILE`
-- CLI flag: [`--notifications-email-tls-ca-cert-file`](../../reference/cli/server.md#--notifications-email-tls-ca-cert-file)
+- CLI flag: [`--notifications-email-tls-ca-cert-file`](../../reference/cli/server/index.md#--notifications-email-tls-ca-cert-file)
 - YAML key: `notifications.email.emailTLS.caCertFile`
 
 ##### Certificate file
@@ -1325,7 +1325,7 @@ Configure TLS for your SMTP server target.
 **Deprecated.** Certificate file to use.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_TLS_CERTFILE`
-- CLI flag: [`--notifications-email-tls-cert-file`](../../reference/cli/server.md#--notifications-email-tls-cert-file)
+- CLI flag: [`--notifications-email-tls-cert-file`](../../reference/cli/server/index.md#--notifications-email-tls-cert-file)
 - YAML key: `notifications.email.emailTLS.certFile`
 
 ##### Certificate key file
@@ -1333,7 +1333,7 @@ Configure TLS for your SMTP server target.
 **Deprecated.** Certificate key file to use.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_TLS_CERTKEYFILE`
-- CLI flag: [`--notifications-email-tls-cert-key-file`](../../reference/cli/server.md#--notifications-email-tls-cert-key-file)
+- CLI flag: [`--notifications-email-tls-cert-key-file`](../../reference/cli/server/index.md#--notifications-email-tls-cert-key-file)
 - YAML key: `notifications.email.emailTLS.certKeyFile`
 
 ##### Server name
@@ -1341,7 +1341,7 @@ Configure TLS for your SMTP server target.
 **Deprecated.** Server name to verify against the target certificate.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_TLS_SERVERNAME`
-- CLI flag: [`--notifications-email-tls-server-name`](../../reference/cli/server.md#--notifications-email-tls-server-name)
+- CLI flag: [`--notifications-email-tls-server-name`](../../reference/cli/server/index.md#--notifications-email-tls-server-name)
 - YAML key: `notifications.email.emailTLS.serverName`
 
 ##### Skip certificate verification (insecure)
@@ -1349,7 +1349,7 @@ Configure TLS for your SMTP server target.
 **Deprecated.** Skip verification of the target server's certificate (insecure).
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_TLS_SKIPVERIFY`
-- CLI flag: [`--notifications-email-tls-skip-verify`](../../reference/cli/server.md#--notifications-email-tls-skip-verify)
+- CLI flag: [`--notifications-email-tls-skip-verify`](../../reference/cli/server/index.md#--notifications-email-tls-skip-verify)
 - YAML key: `notifications.email.emailTLS.insecureSkipVerify`
 
 ##### StartTLS
@@ -1357,7 +1357,7 @@ Configure TLS for your SMTP server target.
 **Deprecated.** Enable STARTTLS to upgrade insecure SMTP connections using TLS.
 
 - Environment variable: `CODER_NOTIFICATIONS_EMAIL_TLS_STARTTLS`
-- CLI flag: [`--notifications-email-tls-starttls`](../../reference/cli/server.md#--notifications-email-tls-starttls)
+- CLI flag: [`--notifications-email-tls-starttls`](../../reference/cli/server/index.md#--notifications-email-tls-starttls)
 - YAML key: `notifications.email.emailTLS.startTLS`
 
 ### Inbox
@@ -1367,7 +1367,7 @@ Configure TLS for your SMTP server target.
 Enable Coder Inbox.
 
 - Environment variable: `CODER_NOTIFICATIONS_INBOX_ENABLED`
-- CLI flag: [`--notifications-inbox-enabled`](../../reference/cli/server.md#--notifications-inbox-enabled)
+- CLI flag: [`--notifications-inbox-enabled`](../../reference/cli/server/index.md#--notifications-inbox-enabled)
 - YAML key: `notifications.inbox.enabled`
 - Default value: `true`
 
@@ -1378,7 +1378,7 @@ Enable Coder Inbox.
 The endpoint to which to send webhooks.
 
 - Environment variable: `CODER_NOTIFICATIONS_WEBHOOK_ENDPOINT`
-- CLI flag: [`--notifications-webhook-endpoint`](../../reference/cli/server.md#--notifications-webhook-endpoint)
+- CLI flag: [`--notifications-webhook-endpoint`](../../reference/cli/server/index.md#--notifications-webhook-endpoint)
 - YAML key: `notifications.webhook.endpoint`
 
 ## OAuth2
@@ -1392,7 +1392,7 @@ Configure OAuth2: GitHub login and user-provisioning, and Coder's own OAuth 2.1
 Allow all logins, setting this option means allowed orgs and teams must be empty.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_ALLOW_EVERYONE`
-- CLI flag: [`--oauth2-github-allow-everyone`](../../reference/cli/server.md#--oauth2-github-allow-everyone)
+- CLI flag: [`--oauth2-github-allow-everyone`](../../reference/cli/server/index.md#--oauth2-github-allow-everyone)
 - YAML key: `oauth2.github.allowEveryone`
 
 #### Allow signups
@@ -1400,7 +1400,7 @@ Allow all logins, setting this option means allowed orgs and teams must be empty
 Whether new users can sign up with GitHub.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_ALLOW_SIGNUPS`
-- CLI flag: [`--oauth2-github-allow-signups`](../../reference/cli/server.md#--oauth2-github-allow-signups)
+- CLI flag: [`--oauth2-github-allow-signups`](../../reference/cli/server/index.md#--oauth2-github-allow-signups)
 - YAML key: `oauth2.github.allowSignups`
 
 #### Allowed orgs
@@ -1408,7 +1408,7 @@ Whether new users can sign up with GitHub.
 Organizations the user must be a member of to Login with GitHub.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_ALLOWED_ORGS`
-- CLI flag: [`--oauth2-github-allowed-orgs`](../../reference/cli/server.md#--oauth2-github-allowed-orgs)
+- CLI flag: [`--oauth2-github-allowed-orgs`](../../reference/cli/server/index.md#--oauth2-github-allowed-orgs)
 - YAML key: `oauth2.github.allowedOrgs`
 
 #### Allowed teams
@@ -1416,7 +1416,7 @@ Organizations the user must be a member of to Login with GitHub.
 Teams inside organizations the user must be a member of to Login with GitHub. Structured as: `<organization-name>/<team-slug>`.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_ALLOWED_TEAMS`
-- CLI flag: [`--oauth2-github-allowed-teams`](../../reference/cli/server.md#--oauth2-github-allowed-teams)
+- CLI flag: [`--oauth2-github-allowed-teams`](../../reference/cli/server/index.md#--oauth2-github-allowed-teams)
 - YAML key: `oauth2.github.allowedTeams`
 
 #### Client ID
@@ -1424,7 +1424,7 @@ Teams inside organizations the user must be a member of to Login with GitHub. St
 Client ID for Login with GitHub.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_CLIENT_ID`
-- CLI flag: [`--oauth2-github-client-id`](../../reference/cli/server.md#--oauth2-github-client-id)
+- CLI flag: [`--oauth2-github-client-id`](../../reference/cli/server/index.md#--oauth2-github-client-id)
 - YAML key: `oauth2.github.clientID`
 
 #### Client secret
@@ -1432,14 +1432,14 @@ Client ID for Login with GitHub.
 Client secret for Login with GitHub.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_CLIENT_SECRET`
-- CLI flag: [`--oauth2-github-client-secret`](../../reference/cli/server.md#--oauth2-github-client-secret)
+- CLI flag: [`--oauth2-github-client-secret`](../../reference/cli/server/index.md#--oauth2-github-client-secret)
 
 #### Default provider enable
 
 Enable the default GitHub OAuth2 provider managed by Coder.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_DEFAULT_PROVIDER_ENABLE`
-- CLI flag: [`--oauth2-github-default-provider-enable`](../../reference/cli/server.md#--oauth2-github-default-provider-enable)
+- CLI flag: [`--oauth2-github-default-provider-enable`](../../reference/cli/server/index.md#--oauth2-github-default-provider-enable)
 - YAML key: `oauth2.github.defaultProviderEnable`
 - Default value: `true`
 
@@ -1448,7 +1448,7 @@ Enable the default GitHub OAuth2 provider managed by Coder.
 Enable device flow for Login with GitHub.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_DEVICE_FLOW`
-- CLI flag: [`--oauth2-github-device-flow`](../../reference/cli/server.md#--oauth2-github-device-flow)
+- CLI flag: [`--oauth2-github-device-flow`](../../reference/cli/server/index.md#--oauth2-github-device-flow)
 - YAML key: `oauth2.github.deviceFlow`
 - Default value: `false`
 
@@ -1457,7 +1457,7 @@ Enable device flow for Login with GitHub.
 Base URL of a GitHub Enterprise deployment to use for Login with GitHub.
 
 - Environment variable: `CODER_OAUTH2_GITHUB_ENTERPRISE_BASE_URL`
-- CLI flag: [`--oauth2-github-enterprise-base-url`](../../reference/cli/server.md#--oauth2-github-enterprise-base-url)
+- CLI flag: [`--oauth2-github-enterprise-base-url`](../../reference/cli/server/index.md#--oauth2-github-enterprise-base-url)
 - YAML key: `oauth2.github.enterpriseBaseURL`
 
 ### Provider
@@ -1467,7 +1467,7 @@ Base URL of a GitHub Enterprise deployment to use for Login with GitHub.
 Enable the OAuth 2.1 authorization server, which lets external applications (such as MCP clients) obtain tokens for Coder on behalf of users. Disabled by default. When disabled, the OAuth2 endpoints and discovery documents return 404.
 
 - Environment variable: `CODER_OAUTH2_PROVIDER_ENABLE`
-- CLI flag: [`--oauth2-provider-enable`](../../reference/cli/server.md#--oauth2-provider-enable)
+- CLI flag: [`--oauth2-provider-enable`](../../reference/cli/server/index.md#--oauth2-provider-enable)
 - YAML key: `oauth2.provider.enable`
 - Default value: `false`
 
@@ -1478,7 +1478,7 @@ Enable the OAuth 2.1 authorization server, which lets external applications (suc
 Automatically creates missing groups from a user's groups claim.
 
 - Environment variable: `CODER_OIDC_GROUP_AUTO_CREATE`
-- CLI flag: [`--oidc-group-auto-create`](../../reference/cli/server.md#--oidc-group-auto-create)
+- CLI flag: [`--oidc-group-auto-create`](../../reference/cli/server/index.md#--oidc-group-auto-create)
 - YAML key: `oidc.enableGroupAutoCreate`
 - Default value: `false`
 
@@ -1487,7 +1487,7 @@ Automatically creates missing groups from a user's groups claim.
 Whether new users can sign up with OIDC.
 
 - Environment variable: `CODER_OIDC_ALLOW_SIGNUPS`
-- CLI flag: [`--oidc-allow-signups`](../../reference/cli/server.md#--oidc-allow-signups)
+- CLI flag: [`--oidc-allow-signups`](../../reference/cli/server/index.md#--oidc-allow-signups)
 - YAML key: `oidc.allowSignups`
 - Default value: `true`
 
@@ -1496,7 +1496,7 @@ Whether new users can sign up with OIDC.
 If provided any group name not in the list will not be allowed to authenticate. This allows for restricting access to a specific set of groups. This filter is applied after the group mapping and before the regex filter.
 
 - Environment variable: `CODER_OIDC_ALLOWED_GROUPS`
-- CLI flag: [`--oidc-allowed-groups`](../../reference/cli/server.md#--oidc-allowed-groups)
+- CLI flag: [`--oidc-allowed-groups`](../../reference/cli/server/index.md#--oidc-allowed-groups)
 - YAML key: `oidc.groupAllowed`
 
 ### Auth URL parameters
@@ -1504,7 +1504,7 @@ If provided any group name not in the list will not be allowed to authenticate.
 OIDC auth URL parameters to pass to the upstream provider.
 
 - Environment variable: `CODER_OIDC_AUTH_URL_PARAMS`
-- CLI flag: [`--oidc-auth-url-params`](../../reference/cli/server.md#--oidc-auth-url-params)
+- CLI flag: [`--oidc-auth-url-params`](../../reference/cli/server/index.md#--oidc-auth-url-params)
 - YAML key: `oidc.authURLParams`
 - Default value: `{"access_type": "offline"}`
 
@@ -1513,7 +1513,7 @@ OIDC auth URL parameters to pass to the upstream provider.
 Pem encoded certificate file to use for oauth2 PKI/JWT authorization. The public certificate that accompanies oidc-client-key-file. A standard x509 certificate is expected.
 
 - Environment variable: `CODER_OIDC_CLIENT_CERT_FILE`
-- CLI flag: [`--oidc-client-cert-file`](../../reference/cli/server.md#--oidc-client-cert-file)
+- CLI flag: [`--oidc-client-cert-file`](../../reference/cli/server/index.md#--oidc-client-cert-file)
 - YAML key: `oidc.oidcClientCertFile`
 
 ### Client ID
@@ -1521,7 +1521,7 @@ Pem encoded certificate file to use for oauth2 PKI/JWT authorization. The public
 Client ID to use for Login with OIDC.
 
 - Environment variable: `CODER_OIDC_CLIENT_ID`
-- CLI flag: [`--oidc-client-id`](../../reference/cli/server.md#--oidc-client-id)
+- CLI flag: [`--oidc-client-id`](../../reference/cli/server/index.md#--oidc-client-id)
 - YAML key: `oidc.clientID`
 
 ### Client key file
@@ -1529,7 +1529,7 @@ Client ID to use for Login with OIDC.
 Pem encoded RSA private key to use for oauth2 PKI/JWT authorization. This can be used instead of oidc-client-secret if your IDP supports it.
 
 - Environment variable: `CODER_OIDC_CLIENT_KEY_FILE`
-- CLI flag: [`--oidc-client-key-file`](../../reference/cli/server.md#--oidc-client-key-file)
+- CLI flag: [`--oidc-client-key-file`](../../reference/cli/server/index.md#--oidc-client-key-file)
 - YAML key: `oidc.oidcClientKeyFile`
 
 ### Client secret
@@ -1537,14 +1537,14 @@ Pem encoded RSA private key to use for oauth2 PKI/JWT authorization. This can be
 Client secret to use for Login with OIDC.
 
 - Environment variable: `CODER_OIDC_CLIENT_SECRET`
-- CLI flag: [`--oidc-client-secret`](../../reference/cli/server.md#--oidc-client-secret)
+- CLI flag: [`--oidc-client-secret`](../../reference/cli/server/index.md#--oidc-client-secret)
 
 ### Email domain
 
 Email domains that clients logging in with OIDC must match.
 
 - Environment variable: `CODER_OIDC_EMAIL_DOMAIN`
-- CLI flag: [`--oidc-email-domain`](../../reference/cli/server.md#--oidc-email-domain)
+- CLI flag: [`--oidc-email-domain`](../../reference/cli/server/index.md#--oidc-email-domain)
 - YAML key: `oidc.emailDomain`
 
 ### Email field
@@ -1552,7 +1552,7 @@ Email domains that clients logging in with OIDC must match.
 OIDC claim field to use as the email.
 
 - Environment variable: `CODER_OIDC_EMAIL_FIELD`
-- CLI flag: [`--oidc-email-field`](../../reference/cli/server.md#--oidc-email-field)
+- CLI flag: [`--oidc-email-field`](../../reference/cli/server/index.md#--oidc-email-field)
 - YAML key: `oidc.emailField`
 - Default value: `email`
 
@@ -1561,7 +1561,7 @@ OIDC claim field to use as the email.
 This field must be set if using the group sync feature and the scope name is not 'groups'. Set to the claim to be used for groups.
 
 - Environment variable: `CODER_OIDC_GROUP_FIELD`
-- CLI flag: [`--oidc-group-field`](../../reference/cli/server.md#--oidc-group-field)
+- CLI flag: [`--oidc-group-field`](../../reference/cli/server/index.md#--oidc-group-field)
 - YAML key: `oidc.groupField`
 
 ### Group mapping
@@ -1569,7 +1569,7 @@ This field must be set if using the group sync feature and the scope name is not
 A map of OIDC group IDs and the group in Coder it should map to. This is useful for when OIDC providers only return group IDs.
 
 - Environment variable: `CODER_OIDC_GROUP_MAPPING`
-- CLI flag: [`--oidc-group-mapping`](../../reference/cli/server.md#--oidc-group-mapping)
+- CLI flag: [`--oidc-group-mapping`](../../reference/cli/server/index.md#--oidc-group-mapping)
 - YAML key: `oidc.groupMapping`
 - Default value: `{}`
 
@@ -1578,7 +1578,7 @@ A map of OIDC group IDs and the group in Coder it should map to. This is useful
 Ignore the email_verified claim from the upstream provider.
 
 - Environment variable: `CODER_OIDC_IGNORE_EMAIL_VERIFIED`
-- CLI flag: [`--oidc-ignore-email-verified`](../../reference/cli/server.md#--oidc-ignore-email-verified)
+- CLI flag: [`--oidc-ignore-email-verified`](../../reference/cli/server/index.md#--oidc-ignore-email-verified)
 - YAML key: `oidc.ignoreEmailVerified`
 
 ### Ignore UserInfo
@@ -1586,7 +1586,7 @@ Ignore the email_verified claim from the upstream provider.
 Ignore the userinfo endpoint and only use the ID token for user information.
 
 - Environment variable: `CODER_OIDC_IGNORE_USERINFO`
-- CLI flag: [`--oidc-ignore-userinfo`](../../reference/cli/server.md#--oidc-ignore-userinfo)
+- CLI flag: [`--oidc-ignore-userinfo`](../../reference/cli/server/index.md#--oidc-ignore-userinfo)
 - YAML key: `oidc.ignoreUserInfo`
 - Default value: `false`
 
@@ -1595,7 +1595,7 @@ Ignore the userinfo endpoint and only use the ID token for user information.
 Issuer URL to use for Login with OIDC.
 
 - Environment variable: `CODER_OIDC_ISSUER_URL`
-- CLI flag: [`--oidc-issuer-url`](../../reference/cli/server.md#--oidc-issuer-url)
+- CLI flag: [`--oidc-issuer-url`](../../reference/cli/server/index.md#--oidc-issuer-url)
 - YAML key: `oidc.issuerURL`
 
 ### Name field
@@ -1603,7 +1603,7 @@ Issuer URL to use for Login with OIDC.
 OIDC claim field to use as the name.
 
 - Environment variable: `CODER_OIDC_NAME_FIELD`
-- CLI flag: [`--oidc-name-field`](../../reference/cli/server.md#--oidc-name-field)
+- CLI flag: [`--oidc-name-field`](../../reference/cli/server/index.md#--oidc-name-field)
 - YAML key: `oidc.nameField`
 - Default value: `name`
 
@@ -1612,7 +1612,7 @@ OIDC claim field to use as the name.
 Optional override of the default redirect url which uses the deployment's access url. Useful in situations where a deployment has more than 1 domain. Using this setting can also break OIDC, so use with caution.
 
 - Environment variable: `CODER_OIDC_REDIRECT_URL`
-- CLI flag: [`--oidc-redirect-url`](../../reference/cli/server.md#--oidc-redirect-url)
+- CLI flag: [`--oidc-redirect-url`](../../reference/cli/server/index.md#--oidc-redirect-url)
 - YAML key: `oidc.oidc-redirect-url`
 
 ### Regex group filter
@@ -1620,7 +1620,7 @@ Optional override of the default redirect url which uses the deployment's access
 If provided any group name not matching the regex is ignored. This allows for filtering out groups that are not needed. This filter is applied after the group mapping.
 
 - Environment variable: `CODER_OIDC_GROUP_REGEX_FILTER`
-- CLI flag: [`--oidc-group-regex-filter`](../../reference/cli/server.md#--oidc-group-regex-filter)
+- CLI flag: [`--oidc-group-regex-filter`](../../reference/cli/server/index.md#--oidc-group-regex-filter)
 - YAML key: `oidc.groupRegexFilter`
 - Default value: `.*`
 
@@ -1629,7 +1629,7 @@ If provided any group name not matching the regex is ignored. This allows for fi
 Scopes to grant when authenticating with OIDC.
 
 - Environment variable: `CODER_OIDC_SCOPES`
-- CLI flag: [`--oidc-scopes`](../../reference/cli/server.md#--oidc-scopes)
+- CLI flag: [`--oidc-scopes`](../../reference/cli/server/index.md#--oidc-scopes)
 - YAML key: `oidc.scopes`
 - Default value: `openid,profile,email`
 
@@ -1638,7 +1638,7 @@ Scopes to grant when authenticating with OIDC.
 If user role sync is enabled, these roles are always included for all authenticated users. The 'member' role is always assigned.
 
 - Environment variable: `CODER_OIDC_USER_ROLE_DEFAULT`
-- CLI flag: [`--oidc-user-role-default`](../../reference/cli/server.md#--oidc-user-role-default)
+- CLI flag: [`--oidc-user-role-default`](../../reference/cli/server/index.md#--oidc-user-role-default)
 - YAML key: `oidc.userRoleDefault`
 
 ### User role field
@@ -1646,7 +1646,7 @@ If user role sync is enabled, these roles are always included for all authentica
 This field must be set if using the user roles sync feature. Set this to the name of the claim used to store the user's role. The roles should be sent as an array of strings.
 
 - Environment variable: `CODER_OIDC_USER_ROLE_FIELD`
-- CLI flag: [`--oidc-user-role-field`](../../reference/cli/server.md#--oidc-user-role-field)
+- CLI flag: [`--oidc-user-role-field`](../../reference/cli/server/index.md#--oidc-user-role-field)
 - YAML key: `oidc.userRoleField`
 
 ### User role mapping
@@ -1654,7 +1654,7 @@ This field must be set if using the user roles sync feature. Set this to the nam
 A map of the OIDC passed in user roles and the groups in Coder it should map to. This is useful if the group names do not match. If mapped to the empty string, the role will ignored.
 
 - Environment variable: `CODER_OIDC_USER_ROLE_MAPPING`
-- CLI flag: [`--oidc-user-role-mapping`](../../reference/cli/server.md#--oidc-user-role-mapping)
+- CLI flag: [`--oidc-user-role-mapping`](../../reference/cli/server/index.md#--oidc-user-role-mapping)
 - YAML key: `oidc.userRoleMapping`
 - Default value: `{}`
 
@@ -1663,7 +1663,7 @@ A map of the OIDC passed in user roles and the groups in Coder it should map to.
 OIDC claim field to use as the username.
 
 - Environment variable: `CODER_OIDC_USERNAME_FIELD`
-- CLI flag: [`--oidc-username-field`](../../reference/cli/server.md#--oidc-username-field)
+- CLI flag: [`--oidc-username-field`](../../reference/cli/server/index.md#--oidc-username-field)
 - YAML key: `oidc.usernameField`
 - Default value: `preferred_username`
 
@@ -1672,7 +1672,7 @@ OIDC claim field to use as the username.
 The text to show on the OpenID Connect sign in button.
 
 - Environment variable: `CODER_OIDC_SIGN_IN_TEXT`
-- CLI flag: [`--oidc-sign-in-text`](../../reference/cli/server.md#--oidc-sign-in-text)
+- CLI flag: [`--oidc-sign-in-text`](../../reference/cli/server/index.md#--oidc-sign-in-text)
 - YAML key: `oidc.signInText`
 - Default value: `OpenID Connect`
 
@@ -1681,7 +1681,7 @@ The text to show on the OpenID Connect sign in button.
 URL pointing to the icon to use on the OpenID Connect login button.
 
 - Environment variable: `CODER_OIDC_ICON_URL`
-- CLI flag: [`--oidc-icon-url`](../../reference/cli/server.md#--oidc-icon-url)
+- CLI flag: [`--oidc-icon-url`](../../reference/cli/server/index.md#--oidc-icon-url)
 - YAML key: `oidc.iconURL`
 
 ### Signups disabled text
@@ -1689,7 +1689,7 @@ URL pointing to the icon to use on the OpenID Connect login button.
 The custom text to show on the error page informing about disabled OIDC signups. Markdown format is supported.
 
 - Environment variable: `CODER_OIDC_SIGNUPS_DISABLED_TEXT`
-- CLI flag: [`--oidc-signups-disabled-text`](../../reference/cli/server.md#--oidc-signups-disabled-text)
+- CLI flag: [`--oidc-signups-disabled-text`](../../reference/cli/server/index.md#--oidc-signups-disabled-text)
 - YAML key: `oidc.signupsDisabledText`
 
 ### Skip OIDC issuer checks (not recommended)
@@ -1697,7 +1697,7 @@ The custom text to show on the error page informing about disabled OIDC signups.
 OIDC issuer urls must match in the request, the id_token 'iss' claim, and in the well-known configuration. This flag disables that requirement, and can lead to an insecure OIDC configuration. It is not recommended to use this flag.
 
 - Environment variable: `CODER_DANGEROUS_OIDC_SKIP_ISSUER_CHECKS`
-- CLI flag: [`--dangerous-oidc-skip-issuer-checks`](../../reference/cli/server.md#--dangerous-oidc-skip-issuer-checks)
+- CLI flag: [`--dangerous-oidc-skip-issuer-checks`](../../reference/cli/server/index.md#--dangerous-oidc-skip-issuer-checks)
 - YAML key: `oidc.dangerousSkipIssuerChecks`
 
 ## Provisioning
@@ -1709,7 +1709,7 @@ Tune the behavior of the provisioner, which is responsible for creating, updatin
 Disable the reuse of Terraform modules cached at template import for all templates. Modules are re-downloaded on every workspace build. Individual templates cannot opt back in.
 
 - Environment variable: `CODER_PROVISIONER_DISABLE_MODULE_CACHE`
-- CLI flag: [`--provisioner-disable-module-cache`](../../reference/cli/server.md#--provisioner-disable-module-cache)
+- CLI flag: [`--provisioner-disable-module-cache`](../../reference/cli/server/index.md#--provisioner-disable-module-cache)
 - YAML key: `provisioning.disableModuleCache`
 - Default value: `false`
 
@@ -1718,7 +1718,7 @@ Disable the reuse of Terraform modules cached at template import for all templat
 Time to force cancel provisioning tasks that are stuck.
 
 - Environment variable: `CODER_PROVISIONER_FORCE_CANCEL_INTERVAL`
-- CLI flag: [`--provisioner-force-cancel-interval`](../../reference/cli/server.md#--provisioner-force-cancel-interval)
+- CLI flag: [`--provisioner-force-cancel-interval`](../../reference/cli/server/index.md#--provisioner-force-cancel-interval)
 - YAML key: `provisioning.forceCancelInterval`
 - Default value: `10m0s`
 
@@ -1727,14 +1727,14 @@ Time to force cancel provisioning tasks that are stuck.
 Pre-shared key to authenticate external provisioner daemons to Coder server.
 
 - Environment variable: `CODER_PROVISIONER_DAEMON_PSK`
-- CLI flag: [`--provisioner-daemon-psk`](../../reference/cli/server.md#--provisioner-daemon-psk)
+- CLI flag: [`--provisioner-daemon-psk`](../../reference/cli/server/index.md#--provisioner-daemon-psk)
 
 ### Provisioner daemons
 
 Number of provisioner daemons to create on start. If builds are stuck in queued state for a long time, consider increasing this.
 
 - Environment variable: `CODER_PROVISIONER_DAEMONS`
-- CLI flag: [`--provisioner-daemons`](../../reference/cli/server.md#--provisioner-daemons)
+- CLI flag: [`--provisioner-daemons`](../../reference/cli/server/index.md#--provisioner-daemons)
 - YAML key: `provisioning.daemons`
 - Default value: `3`
 
@@ -1743,7 +1743,7 @@ Number of provisioner daemons to create on start. If builds are stuck in queued
 **Deprecated** and ignored.
 
 - Environment variable: `CODER_PROVISIONER_DAEMON_POLL_INTERVAL`
-- CLI flag: [`--provisioner-daemon-poll-interval`](../../reference/cli/server.md#--provisioner-daemon-poll-interval)
+- CLI flag: [`--provisioner-daemon-poll-interval`](../../reference/cli/server/index.md#--provisioner-daemon-poll-interval)
 - YAML key: `provisioning.daemonPollInterval`
 - Default value: `1s`
 
@@ -1752,7 +1752,7 @@ Number of provisioner daemons to create on start. If builds are stuck in queued
 **Deprecated** and ignored.
 
 - Environment variable: `CODER_PROVISIONER_DAEMON_POLL_JITTER`
-- CLI flag: [`--provisioner-daemon-poll-jitter`](../../reference/cli/server.md#--provisioner-daemon-poll-jitter)
+- CLI flag: [`--provisioner-daemon-poll-jitter`](../../reference/cli/server/index.md#--provisioner-daemon-poll-jitter)
 - YAML key: `provisioning.daemonPollJitter`
 - Default value: `100ms`
 
@@ -1765,7 +1765,7 @@ Configure data retention policies for various database tables. Retention policie
 How long expired API keys are retained before being deleted. Keeping expired keys allows the backend to return a more helpful error when a user tries to use an expired key. Set to 0 to disable automatic deletion of expired keys.
 
 - Environment variable: `CODER_API_KEYS_RETENTION`
-- CLI flag: [`--api-keys-retention`](../../reference/cli/server.md#--api-keys-retention)
+- CLI flag: [`--api-keys-retention`](../../reference/cli/server/index.md#--api-keys-retention)
 - YAML key: `retention.api_keys`
 - Default value: `7d`
 
@@ -1774,7 +1774,7 @@ How long expired API keys are retained before being deleted. Keeping expired key
 How long audit log entries are retained. Set to 0 to disable (keep indefinitely). We advise keeping audit logs for at least a year, and in accordance with your compliance requirements.
 
 - Environment variable: `CODER_AUDIT_LOGS_RETENTION`
-- CLI flag: [`--audit-logs-retention`](../../reference/cli/server.md#--audit-logs-retention)
+- CLI flag: [`--audit-logs-retention`](../../reference/cli/server/index.md#--audit-logs-retention)
 - YAML key: `retention.audit_logs`
 - Default value: `0`
 
@@ -1783,7 +1783,7 @@ How long audit log entries are retained. Set to 0 to disable (keep indefinitely)
 How long boundary audit log entries are retained. Boundary logs record HTTP requests processed by a Boundary confinement proxy. Set to 0 to disable automatic deletion (keep indefinitely). Adjust to match your organization's regulatory requirements.
 
 - Environment variable: `CODER_BOUNDARY_LOG_RETENTION`
-- CLI flag: [`--boundary-log-retention`](../../reference/cli/server.md#--boundary-log-retention)
+- CLI flag: [`--boundary-log-retention`](../../reference/cli/server/index.md#--boundary-log-retention)
 - YAML key: `retention.boundary_logs`
 - Default value: `0`
 
@@ -1792,7 +1792,7 @@ How long boundary audit log entries are retained. Boundary logs record HTTP requ
 How long connection log entries are retained. Set to 0 to disable (keep indefinitely).
 
 - Environment variable: `CODER_CONNECTION_LOGS_RETENTION`
-- CLI flag: [`--connection-logs-retention`](../../reference/cli/server.md#--connection-logs-retention)
+- CLI flag: [`--connection-logs-retention`](../../reference/cli/server/index.md#--connection-logs-retention)
 - YAML key: `retention.connection_logs`
 - Default value: `0`
 
@@ -1801,7 +1801,7 @@ How long connection log entries are retained. Set to 0 to disable (keep indefini
 How long workspace agent logs are retained. Logs from non-latest builds are deleted if the agent hasn't connected within this period. Logs from the latest build are always retained. Set to 0 to disable automatic deletion.
 
 - Environment variable: `CODER_WORKSPACE_AGENT_LOGS_RETENTION`
-- CLI flag: [`--workspace-agent-logs-retention`](../../reference/cli/server.md#--workspace-agent-logs-retention)
+- CLI flag: [`--workspace-agent-logs-retention`](../../reference/cli/server/index.md#--workspace-agent-logs-retention)
 - YAML key: `retention.workspace_agent_logs`
 - Default value: `7d`
 
@@ -1814,7 +1814,7 @@ Telemetry is critical to our ability to improve Coder. We strip all personal inf
 Whether telemetry is enabled or not. Coder collects anonymized usage data to help improve our product.
 
 - Environment variable: `CODER_TELEMETRY_ENABLE`
-- CLI flag: [`--telemetry`](../../reference/cli/server.md#--telemetry)
+- CLI flag: [`--telemetry`](../../reference/cli/server/index.md#--telemetry)
 - YAML key: `telemetry.enable`
 - Default value: `true`
 
@@ -1825,7 +1825,7 @@ Whether telemetry is enabled or not. Coder collects anonymized usage data to hel
 Disable the template builder feature for guided template creation. When disabled, all /api/v2/templatebuilder/* endpoints return 404.
 
 - Environment variable: `CODER_DISABLE_TEMPLATE_BUILDER`
-- CLI flag: [`--disable-template-builder`](../../reference/cli/server.md#--disable-template-builder)
+- CLI flag: [`--disable-template-builder`](../../reference/cli/server/index.md#--disable-template-builder)
 - YAML key: `templateBuilder.disabled`
 
 ### Registry URL
@@ -1833,7 +1833,7 @@ Disable the template builder feature for guided template creation. When disabled
 The module registry host the template builder uses for module source paths (for example, "registry.coder.com" or "mirror.internal:8443"). An http(s):// scheme and trailing slash are stripped; a path, query, fragment, or credentials is rejected.
 
 - Environment variable: `CODER_TEMPLATE_BUILDER_REGISTRY_URL`
-- CLI flag: [`--template-builder-registry-url`](../../reference/cli/server.md#--template-builder-registry-url)
+- CLI flag: [`--template-builder-registry-url`](../../reference/cli/server/index.md#--template-builder-registry-url)
 - YAML key: `templateBuilder.registryURL`
 - Default value: `registry.coder.com`
 
@@ -1846,7 +1846,7 @@ Allow users to set quiet hours schedules each day for workspaces to avoid worksp
 Allow users to set their own quiet hours schedule for workspaces to stop in (depending on template autostop requirement settings). If false, users can't change their quiet hours schedule and the site default is always used.
 
 - Environment variable: `CODER_ALLOW_CUSTOM_QUIET_HOURS`
-- CLI flag: [`--allow-custom-quiet-hours`](../../reference/cli/server.md#--allow-custom-quiet-hours)
+- CLI flag: [`--allow-custom-quiet-hours`](../../reference/cli/server/index.md#--allow-custom-quiet-hours)
 - YAML key: `userQuietHoursSchedule.allowCustomQuietHours`
 - Default value: `true`
 
@@ -1855,7 +1855,7 @@ Allow users to set their own quiet hours schedule for workspaces to stop in (dep
 The default daily cron schedule applied to users that haven't set a custom quiet hours schedule themselves. The quiet hours schedule determines when workspaces will be force stopped due to the template's autostop requirement, and will round the max deadline up to be within the user's quiet hours window (or default). The format is the same as the standard cron format, but the day-of-month, month and day-of-week must be *. Only one hour and minute can be specified (ranges or comma separated values are not supported).
 
 - Environment variable: `CODER_QUIET_HOURS_DEFAULT_SCHEDULE`
-- CLI flag: [`--default-quiet-hours-schedule`](../../reference/cli/server.md#--default-quiet-hours-schedule)
+- CLI flag: [`--default-quiet-hours-schedule`](../../reference/cli/server/index.md#--default-quiet-hours-schedule)
 - YAML key: `userQuietHoursSchedule.defaultQuietHoursSchedule`
 - Default value: `CRON_TZ=UTC 0 0 * * *`
 
@@ -1868,7 +1868,7 @@ Configure how workspace prebuilds behave.
 How often to reconcile workspace prebuilds state.
 
 - Environment variable: `CODER_WORKSPACE_PREBUILDS_RECONCILIATION_INTERVAL`
-- CLI flag: [`--workspace-prebuilds-reconciliation-interval`](../../reference/cli/server.md#--workspace-prebuilds-reconciliation-interval)
+- CLI flag: [`--workspace-prebuilds-reconciliation-interval`](../../reference/cli/server/index.md#--workspace-prebuilds-reconciliation-interval)
 - YAML key: `workspace_prebuilds.reconciliation_interval`
 - Default value: `1m0s`
 
@@ -1882,11 +1882,11 @@ How often to reconcile workspace prebuilds state.
 Allow workspace apps that are not served from subdomains to be shared. Path-based app sharing is DISABLED by default for security purposes. Path-based apps can make requests to the Coder API and pose a security risk when the workspace serves malicious JavaScript. Path-based apps can be disabled entirely with --disable-path-apps for further security.
 
 - Environment variable: `CODER_DANGEROUS_ALLOW_PATH_APP_SHARING`
-- CLI flag: [`--dangerous-allow-path-app-sharing`](../../reference/cli/server.md#--dangerous-allow-path-app-sharing)
+- CLI flag: [`--dangerous-allow-path-app-sharing`](../../reference/cli/server/index.md#--dangerous-allow-path-app-sharing)
 
 ### Allow site owners to access path apps
 
 Allow site-owners to access workspace apps from workspaces they do not own. Owners cannot access path-based apps they do not own by default. Path-based apps can make requests to the Coder API and pose a security risk when the workspace serves malicious JavaScript. Path-based apps can be disabled entirely with --disable-path-apps for further security.
 
 - Environment variable: `CODER_DANGEROUS_ALLOW_PATH_APP_SITE_OWNER_ACCESS`
-- CLI flag: [`--dangerous-allow-path-app-site-owner-access`](../../reference/cli/server.md#--dangerous-allow-path-app-site-owner-access)
+- CLI flag: [`--dangerous-allow-path-app-site-owner-access`](../../reference/cli/server/index.md#--dangerous-allow-path-app-site-owner-access)
diff --git a/docs/admin/setup/index.md b/docs/admin/setup/index.md
index dd03b72dbd..03e4e4a187 100644
--- a/docs/admin/setup/index.md
+++ b/docs/admin/setup/index.md
@@ -4,7 +4,7 @@ title: Configure control plane access
 
 The control plane's primary configuration is done via environment variables. For
 a full list of the options, run `coder server --help` or see our
-[CLI documentation](../../reference/cli/server.md).
+[CLI documentation](../../reference/cli/server/index.md).
 
 > [!TIP]
 > Need to look up an exact environment variable, CLI flag, or YAML key for a
@@ -65,8 +65,8 @@ If you are providing TLS certificates directly to the control plane, either
 1. Configure multiple certificates and keys via
    [`coder.tls.secretNames`](../../../helm/coder/values.yaml)
    in the Helm Chart, or
-   [`--tls-cert-file`](../../reference/cli/server.md#--tls-cert-file) and
-   [`--tls-key-file`](../../reference/cli/server.md#--tls-key-file) command line
+   [`--tls-cert-file`](../../reference/cli/server/index.md#--tls-cert-file) and
+   [`--tls-key-file`](../../reference/cli/server/index.md#--tls-key-file) command line
    options (these both take a comma separated list of files; list certificates
    and their respective keys in the same order).
 
diff --git a/docs/admin/templates/creating-templates.md b/docs/admin/templates/creating-templates.md
index 647248113b..d2b9fb51af 100644
--- a/docs/admin/templates/creating-templates.md
+++ b/docs/admin/templates/creating-templates.md
@@ -102,7 +102,7 @@ The template builder's first step also links to alternative creation paths:
 
 You can use the [Coder CLI](../../install/cli.md) to manage templates for Coder.
 
-After [logging in](../../reference/cli/login.md) to your deployment, create a
+After [logging in](../../reference/cli/login/index.md) to your deployment, create a
 folder to store your templates:
 
 ```sh
@@ -111,7 +111,7 @@ mkdir $HOME/coder-templates
 cd $HOME/coder-templates
 ```
 
-Use the [`templates init`](../../reference/cli/templates_init.md) command to
+Use the [`templates init`](../../reference/cli/templates/init.md) command to
 pull a starter template:
 
 ```sh
@@ -128,7 +128,7 @@ cd universal-template
 ```
 
 Next, push it to Coder with the
-[`templates push`](../../reference/cli/templates_push.md) command:
+[`templates push`](../../reference/cli/templates/push.md) command:
 
 ```sh
 coder templates push
@@ -139,7 +139,7 @@ infrastructure in the given location. Learn how to configure
 [provisioner authentication](../../install/operate/provisioners/index.md).
 
 You can edit the metadata of the template such as the display name with the
-[`templates edit`](../../reference/cli/templates_edit.md) command:
+[`templates edit`](../../reference/cli/templates/edit.md) command:
 
 ```sh
 coder templates edit universal-template \
diff --git a/docs/admin/templates/extending-templates/agent-metadata.md b/docs/admin/templates/extending-templates/agent-metadata.md
index 8e5e8caf87..8c5ec70e95 100644
--- a/docs/admin/templates/extending-templates/agent-metadata.md
+++ b/docs/admin/templates/extending-templates/agent-metadata.md
@@ -17,7 +17,7 @@ All of these examples use
 for the script declaration. With heredoc strings, you can script without messy
 escape codes, just as if you were working in your terminal.
 
-Some of the examples use the [`coder stat`](../../../reference/cli/stat.md)
+Some of the examples use the [`coder stat`](../../../reference/cli/stat/index.md)
 command. This is useful for determining CPU and memory usage of the VM or
 container that the workspace is running in, which is more accurate than resource
 usage about the workspace's host.
diff --git a/docs/admin/templates/extending-templates/prebuilt-workspaces.md b/docs/admin/templates/extending-templates/prebuilt-workspaces.md
index e76b55238e..15a1534225 100644
--- a/docs/admin/templates/extending-templates/prebuilt-workspaces.md
+++ b/docs/admin/templates/extending-templates/prebuilt-workspaces.md
@@ -450,16 +450,16 @@ Because the condition evaluates based on the workspace owner, provisioning or de
 
 #### Validation
 
-To confirm that prebuild jobs are correctly routed to the new provisioner pool, use the Provisioner Jobs dashboard or the [`coder provisioner jobs list`](../../../reference/cli/provisioner_jobs_list.md) CLI command to inspect job metadata and tags.
+To confirm that prebuild jobs are correctly routed to the new provisioner pool, use the Provisioner Jobs dashboard or the [`coder provisioner jobs list`](../../../reference/cli/provisioner/jobs/list.md) CLI command to inspect job metadata and tags.
 Follow these steps:
 
 1. Publish the new template version.
 
 1. Validate the status of the prebuild provisioners.
-    Check the Provisioners page in the Coder dashboard or run the [`coder provisioner list`](../../../reference/cli/provisioner_list.md) CLI command to ensure all prebuild provisioners are up to date and the tags are properly set.
+    Check the Provisioners page in the Coder dashboard or run the [`coder provisioner list`](../../../reference/cli/provisioner/list.md) CLI command to ensure all prebuild provisioners are up to date and the tags are properly set.
 
 1. Wait for the prebuilds reconciliation loop to run.
-    The loop frequency is controlled by the configuration value [`CODER_WORKSPACE_PREBUILDS_RECONCILIATION_INTERVAL`](../../../reference/cli/server.md#--workspace-prebuilds-reconciliation-interval).
+    The loop frequency is controlled by the configuration value [`CODER_WORKSPACE_PREBUILDS_RECONCILIATION_INTERVAL`](../../../reference/cli/server/index.md#--workspace-prebuilds-reconciliation-interval).
     When the loop runs, it will provision prebuilds for the new template version and deprovision prebuilds for the previous version.
     Both provisioning and deprovisioning jobs for prebuilds should display the tag `is_prebuild=true`.
 
diff --git a/docs/admin/templates/extending-templates/web-ides.md b/docs/admin/templates/extending-templates/web-ides.md
index 064555073e..ac21c6f056 100644
--- a/docs/admin/templates/extending-templates/web-ides.md
+++ b/docs/admin/templates/extending-templates/web-ides.md
@@ -216,7 +216,7 @@ module "jupyter" {
 If you cannot enable a
 [wildcard subdomain](../../../admin/setup/index.md#wildcard-access-url), you can
 configure the template to run Jupyter on a path. There is however
-[security risk](../../../reference/cli/server.md#--dangerous-allow-path-app-sharing)
+[security risk](../../../reference/cli/server/index.md#--dangerous-allow-path-app-sharing)
 running an app on a path and the template code is more complicated with coder
 value substitution to recreate the path structure.
 
diff --git a/docs/admin/templates/managing-templates/change-management.md b/docs/admin/templates/managing-templates/change-management.md
index 85fc51cc4e..3ba719e51b 100644
--- a/docs/admin/templates/managing-templates/change-management.md
+++ b/docs/admin/templates/managing-templates/change-management.md
@@ -7,7 +7,7 @@ automating the creation of new versions in CI/CD pipelines.
 
 These pipelines will require tokens for your deployment. To cap token lifetime
 on creation,
-[configure the control plane to set a shorter max token lifetime](../../../reference/cli/server.md#--max-token-lifetime).
+[configure the control plane to set a shorter max token lifetime](../../../reference/cli/server/index.md#--max-token-lifetime).
 
 ## coderd Terraform Provider
 
@@ -100,6 +100,6 @@ for an example of how to test and publish Coder templates in a CI/CD pipeline.
 
 ### Next steps
 
-- [Coder CLI Reference](../../../reference/cli/templates.md)
+- [Coder CLI Reference](../../../reference/cli/templates/index.md)
 - [Coderd Terraform Provider Reference](https://registry.terraform.io/providers/coder/coderd/latest/docs)
 - [Coderd API Reference](../../../reference/index.md)
diff --git a/docs/admin/templates/managing-templates/dependencies.md b/docs/admin/templates/managing-templates/dependencies.md
index e1eb169799..b5afa3dc74 100644
--- a/docs/admin/templates/managing-templates/dependencies.md
+++ b/docs/admin/templates/managing-templates/dependencies.md
@@ -93,7 +93,7 @@ inside a folder containing the Terraform source code for a given template.
 
 This will create a new file named `.terraform.lock.hcl` in the current
 directory. When you next run
-[`coder templates push`](../../../reference/cli/templates_push.md), the lock
+[`coder templates push`](../../../reference/cli/templates/push.md), the lock
 file will be stored alongside with the other template source code.
 
 > [!NOTE]
diff --git a/docs/admin/templates/managing-templates/schedule.md b/docs/admin/templates/managing-templates/schedule.md
index 1c5aac6dd0..caac23f2f7 100644
--- a/docs/admin/templates/managing-templates/schedule.md
+++ b/docs/admin/templates/managing-templates/schedule.md
@@ -108,7 +108,7 @@ stopped due to the policy at the start of the user's quiet hours.
 ![User schedule settings](../../../images/admin/templates/schedule/user-quiet-hours.png)
 
 Admins can define the default quiet hours for all users with the
-[CODER_QUIET_HOURS_DEFAULT_SCHEDULE](../../../reference/cli/server.md#--default-quiet-hours-schedule)
+[CODER_QUIET_HOURS_DEFAULT_SCHEDULE](../../../reference/cli/server/index.md#--default-quiet-hours-schedule)
 environment variable. The value should be a cron expression such as
 `CRON_TZ=America/Chicago 30 2 * * *` which would set the default quiet hours to
 2:30 AM in the America/Chicago timezone. The cron schedule can only have a
@@ -117,7 +117,7 @@ to set the default quiet hours to a time when most users are not expected to be
 using Coder.
 
 Admins can force users to use the default quiet hours with the
-[CODER_ALLOW_CUSTOM_QUIET_HOURS](../../../reference/cli/server.md#--allow-custom-quiet-hours)
+[CODER_ALLOW_CUSTOM_QUIET_HOURS](../../../reference/cli/server/index.md#--allow-custom-quiet-hours)
 environment variable. Users will still be able to see the page, but will be
 unable to set a custom time or timezone. If users have already set a custom
 quiet hours schedule, it will be ignored and the default will be used instead.
diff --git a/docs/admin/templates/startup-coordination/usage.md b/docs/admin/templates/startup-coordination/usage.md
index ce21f104c7..89eae7850b 100644
--- a/docs/admin/templates/startup-coordination/usage.md
+++ b/docs/admin/templates/startup-coordination/usage.md
@@ -121,7 +121,7 @@ Before rolling out to all users:
 3. Verify all units reach "completed" status using `coder exp sync list`
 4. Test workspace functionality
 
-Once you're satisfied, [promote the new template version](../../../reference/cli/templates_versions_promote.md).
+Once you're satisfied, [promote the new template version](../../../reference/cli/templates/versions/promote.md).
 
 ### Handle missing CLI gracefully
 
diff --git a/docs/admin/users/github-auth.md b/docs/admin/users/github-auth.md
index 272ce09534..5d86b4df0d 100644
--- a/docs/admin/users/github-auth.md
+++ b/docs/admin/users/github-auth.md
@@ -49,7 +49,7 @@ To use the default configuration:
 ## Disable the Default GitHub App
 
 You can disable the default GitHub app by [configuring your own app](#step-1-configure-the-oauth-application-in-github)
-or by adding the following environment variable to your [control plane configuration](../../reference/cli/server.md#options):
+or by adding the following environment variable to your [control plane configuration](../../reference/cli/server/index.md#options):
 
 ```sh
 CODER_OAUTH2_GITHUB_DEFAULT_PROVIDER_ENABLE=false
@@ -69,7 +69,7 @@ CODER_OAUTH2_GITHUB_DEFAULT_PROVIDER_ENABLE=false
 1. GitHub will ask you for the following Coder parameters:
 
    - **Homepage URL**: Set to your Coder deployment's
-     [`CODER_ACCESS_URL`](../../reference/cli/server.md#--access-url) (e.g.
+     [`CODER_ACCESS_URL`](../../reference/cli/server/index.md#--access-url) (e.g.
      `https://coder.domain.com`)
    - **User Authorization Callback URL**: Set to `https://coder.domain.com`
 
diff --git a/docs/admin/users/groups-roles.md b/docs/admin/users/groups-roles.md
index 5d611b9f25..04cce5f52e 100644
--- a/docs/admin/users/groups-roles.md
+++ b/docs/admin/users/groups-roles.md
@@ -48,7 +48,7 @@ Refer to [Default member roles](./organizations.md#default-member-roles) for how
 The preceding table describes a default deployment.
 A deployment that sets `CODER_DISABLE_OWNER_WORKSPACE_ACCESS` removes the Owner role's SSH, application, and terminal access to other users' workspaces.
 Owners keep that access to workspaces they own.
-Refer to [`--disable-owner-workspace-access`](../../reference/cli/server.md#--disable-owner-workspace-access) for the flag, environment variable, and YAML forms.
+Refer to [`--disable-owner-workspace-access`](../../reference/cli/server/index.md#--disable-owner-workspace-access) for the flag, environment variable, and YAML forms.
 
 ## Organization roles
 
diff --git a/docs/admin/users/idp-sync.md b/docs/admin/users/idp-sync.md
index ec9e1548c6..8087caf8bc 100644
--- a/docs/admin/users/idp-sync.md
+++ b/docs/admin/users/idp-sync.md
@@ -39,7 +39,7 @@ If your OpenID Connect provider supports group claims, you can configure Coder
 to synchronize groups in your auth provider to groups within Coder. To enable
 group sync, ensure that the `groups` claim is being sent by your OpenID
 provider. You might need to request an additional
-[scope](../../reference/cli/server.md#--oidc-scopes) or additional configuration
+[scope](../../reference/cli/server/index.md#--oidc-scopes) or additional configuration
 on the OpenID provider side.
 
 If group sync is enabled, the user's groups will be controlled by the OIDC
@@ -151,7 +151,7 @@ Visit the Coder UI to confirm these changes:
 > You can use the dashboard to configure group sync instead.
 
 1. Configure the control plane to read groups from the claim name with the
-   [OIDC group field](../../reference/cli/server.md#--oidc-group-field) server
+   [OIDC group field](../../reference/cli/server/index.md#--oidc-group-field) server
    flag:
 
    - Environment variable:
@@ -172,7 +172,7 @@ Visit the Coder UI to confirm these changes:
 1. For cases when an OIDC provider only returns group IDs or you want to have
    different group names in Coder than in your OIDC provider, you can configure
    mapping between the two with the
-   [OIDC group mapping](../../reference/cli/server.md#--oidc-group-mapping) server
+   [OIDC group mapping](../../reference/cli/server/index.md#--oidc-group-mapping) server
    flag:
 
    - Environment variable:
@@ -205,7 +205,7 @@ Visit the Coder UI to confirm these changes:
 ### Group allowlist
 
 You can limit which groups from your identity provider can log in to Coder with
-[CODER_OIDC_ALLOWED_GROUPS](../../reference/cli/server.md#--oidc-allowed-groups).
+[CODER_OIDC_ALLOWED_GROUPS](../../reference/cli/server/index.md#--oidc-allowed-groups).
 Users who are not in a matching group will see the following error:
 
 <img height="412px" src="../../images/admin/group-allowlist.png" alt="Unauthorized group error" align="center" />
@@ -298,7 +298,7 @@ Visit the Coder UI to confirm these changes:
 > You can use the dashboard to configure role sync instead.
 
 1. Configure the control plane to read groups from the claim name with the
-   [OIDC role field](../../reference/cli/server.md#--oidc-user-role-field)
+   [OIDC role field](../../reference/cli/server/index.md#--oidc-user-role-field)
    server flag:
 
 1. Set the following in your control plane [configuration](../setup/index.md).
diff --git a/docs/admin/users/index.md b/docs/admin/users/index.md
index 14bedd3fd0..0c5bc0dcb6 100644
--- a/docs/admin/users/index.md
+++ b/docs/admin/users/index.md
@@ -250,7 +250,7 @@ coder users list --output json | \
   jq -r '["username","email","created_at","status"], (.[] | [.username, .email, .created_at, .status]) | @csv' > users.csv
 ```
 
-Visit the [users list](../../reference/cli/users_list.md) documentation for more options.
+Visit the [users list](../../reference/cli/users/list.md) documentation for more options.
 
 ### API
 
diff --git a/docs/admin/users/oidc-auth/refresh-tokens.md b/docs/admin/users/oidc-auth/refresh-tokens.md
index 54bf4a5649..8cf5d73336 100644
--- a/docs/admin/users/oidc-auth/refresh-tokens.md
+++ b/docs/admin/users/oidc-auth/refresh-tokens.md
@@ -35,7 +35,7 @@ Go to the Azure Portal > **Azure Active Directory** > **App registrations** > Yo
    - Verify a Client secret (or certificate) is valid.
      Coder uses it to redeem refresh tokens.
 
-1. In your [Coder configuration](../../../reference/cli/server.md#--oidc-auth-url-params), request the same scopes:
+1. In your [Coder configuration](../../../reference/cli/server/index.md#--oidc-auth-url-params), request the same scopes:
 
    ```dotenv
    CODER_OIDC_SCOPES=openid,profile,email,offline_access
@@ -60,7 +60,7 @@ To ensure Coder receives a refresh token when users authenticate with Google dir
 in the auth URL parameters (`CODER_OIDC_AUTH_URL_PARAMS`).
 Without this, users will be logged out when their access token expires.
 
-In your [Coder configuration](../../../reference/cli/server.md#--oidc-auth-url-params):
+In your [Coder configuration](../../../reference/cli/server/index.md#--oidc-auth-url-params):
 
 ```dotenv
 CODER_OIDC_SCOPES=openid,profile,email
@@ -76,7 +76,7 @@ This means that when a user authenticates using OIDC, the application requests o
 including the ability to refresh access tokens without requiring the user to reauthenticate.
 
 Add the `offline_access` scope to enable refresh tokens in your
-[Coder configuration](../../../reference/cli/server.md#--oidc-auth-url-params):
+[Coder configuration](../../../reference/cli/server/index.md#--oidc-auth-url-params):
 
 ```dotenv
 CODER_OIDC_SCOPES=openid,profile,email,offline_access
@@ -99,7 +99,7 @@ CODER_OIDC_AUTH_URL_PARAMS='{"access_type":"offline"}'
 
 1. Save your changes in PingFederate.
 
-1. In your [Coder configuration](../../../reference/cli/server.md#--oidc-scopes), add the `offline_access` scope:
+1. In your [Coder configuration](../../../reference/cli/server/index.md#--oidc-scopes), add the `offline_access` scope:
 
    ```dotenv
    CODER_OIDC_SCOPES=openid,profile,email,offline_access
diff --git a/docs/admin/users/password-auth.md b/docs/admin/users/password-auth.md
index 03f3fa896e..e4e3c5e5a4 100644
--- a/docs/admin/users/password-auth.md
+++ b/docs/admin/users/password-auth.md
@@ -8,13 +8,13 @@ setup is a username/password account.
 ## Disable password authentication
 
 To disable password authentication, use the
-[`CODER_DISABLE_PASSWORD_AUTH`](../../reference/cli/server.md#--disable-password-auth)
+[`CODER_DISABLE_PASSWORD_AUTH`](../../reference/cli/server/index.md#--disable-password-auth)
 flag on the control plane.
 
 ## Restore the `Owner` user
 
 If you remove the admin user account (or forget the password), you can run the
-[`coder server create-admin-user`](../../reference/cli/server_create-admin-user.md)command
+[`coder server create-admin-user`](../../reference/cli/server/create-admin-user.md)command
 on your server.
 
 > [!IMPORTANT]
diff --git a/docs/admin/users/sessions-tokens.md b/docs/admin/users/sessions-tokens.md
index 8f227b2393..acbbd80aab 100644
--- a/docs/admin/users/sessions-tokens.md
+++ b/docs/admin/users/sessions-tokens.md
@@ -29,7 +29,7 @@ export CODER_SESSION_TOKEN=$(coder login token)
 ### Session Durations
 
 By default, sessions last 24&nbsp;hours and are automatically refreshed.
-You can configure [`CODER_SESSION_DURATION`](../../reference/cli/server.md#--session-duration) to change the duration and [`CODER_DISABLE_SESSION_EXPIRY_REFRESH`](../../reference/cli/server.md#--disable-session-expiry-refresh) to configure this behavior.
+You can configure [`CODER_SESSION_DURATION`](../../reference/cli/server/index.md#--session-duration) to change the duration and [`CODER_DISABLE_SESSION_EXPIRY_REFRESH`](../../reference/cli/server/index.md#--disable-session-expiry-refresh) to configure this behavior.
 
 ## Long-Lived Tokens (API Tokens)
 
@@ -60,7 +60,7 @@ coder tokens create --name=my-token --lifetime=720h
 ```
 
 See the help docs for
-[`coder tokens create`](../../reference/cli/tokens_create.md) for more info.
+[`coder tokens create`](../../reference/cli/tokens/create.md) for more info.
 
 </div>
 
@@ -80,7 +80,7 @@ coder tokens create --name my-token --user <username>
 ```
 
 See the full CLI reference for
-[`coder tokens create`](../../reference/cli/tokens_create.md)
+[`coder tokens create`](../../reference/cli/tokens/create.md)
 
 #### API
 
@@ -92,7 +92,7 @@ Use our API reference for more information on how to
 ### Set max token length
 
 You can use the
-[`CODER_MAX_TOKEN_LIFETIME`](../../reference/cli/server.md#--max-token-lifetime)
+[`CODER_MAX_TOKEN_LIFETIME`](../../reference/cli/server/index.md#--max-token-lifetime)
 server flag to set the maximum duration for long-lived tokens in your
 deployment.
 
diff --git a/docs/ai-coder/agents/licensing-usage.md b/docs/ai-coder/agents/licensing-usage.md
index 5e9ef9c582..caba197b38 100644
--- a/docs/ai-coder/agents/licensing-usage.md
+++ b/docs/ai-coder/agents/licensing-usage.md
@@ -65,7 +65,7 @@ Coder generates one `hb_agent_runtime_v1` event for each UTC hour shortly after
 In steady state, each hour's usage typically reaches Tallyman within about 25&nbsp;minutes of the hour closing.
 You can monitor these requests in `coderd` logs.
 
-A successful request produces a debug log similar to the following example when you enable debug logging with [`CODER_LOG_FILTER=.*`](../../reference/cli/server.md#-l---log-filter):
+A successful request produces a debug log similar to the following example when you enable debug logging with [`CODER_LOG_FILTER=.*`](../../reference/cli/server/index.md#-l---log-filter):
 
 ```sh
 [debu] published usage events to tallyman accepted=1 rejected=0
diff --git a/docs/ai-coder/ai-gateway/ai-gateway-proxy/setup.md b/docs/ai-coder/ai-gateway/ai-gateway-proxy/setup.md
index 63539713f7..c921c8af2e 100644
--- a/docs/ai-coder/ai-gateway/ai-gateway-proxy/setup.md
+++ b/docs/ai-coder/ai-gateway/ai-gateway-proxy/setup.md
@@ -53,7 +53,7 @@ All other traffic is tunneled through without decryption.
 
 ### Proxy target
 
-Intercepted requests are forwarded to the AI Gateway, configured via [`CODER_AI_GATEWAY_PROXY_TARGET`](../../../reference/cli/server.md#--ai-gateway-proxy-target).
+Intercepted requests are forwarded to the AI Gateway, configured via [`CODER_AI_GATEWAY_PROXY_TARGET`](../../../reference/cli/server/index.md#--ai-gateway-proxy-target).
 By default, this is the embedded AI Gateway at `<coderd-access-url>/api/v2/ai-gateway`, and no configuration is needed.
 
 AI Gateway Proxy remains part of the `coderd` process when you [deploy AI Gateway as a standalone service](../standalone.md).
@@ -67,7 +67,7 @@ CODER_AI_GATEWAY_PROXY_TARGET=https://ai-gateway.example.com/
 
 The target is used as-is: the proxy appends only the provider and request path to it, and the URL must not include query parameters.
 
-For additional configuration options, see the [`coder server` configuration](../../../reference/cli/server.md#options).
+For additional configuration options, see the [`coder server` configuration](../../../reference/cli/server/index.md#options).
 
 ## Security Considerations
 
@@ -98,7 +98,7 @@ The IP validation and TCP connect happen atomically, preventing DNS rebinding at
 To prevent unauthorized use, restrict network access to the proxy so that only authorized clients can connect.
 
 In case the AI Gateway [proxy target](#proxy-target) hostname (the Coder access URL by default) resolves to a private address, it is automatically exempt from this restriction so the proxy can always reach the configured AI Gateway.
-If you need to allow access to additional internal networks via the proxy, use the Allowlist CIDRs option ([`CODER_AI_GATEWAY_PROXY_ALLOWED_PRIVATE_CIDRS`](../../../reference/cli/server.md#--ai-gateway-proxy-allowed-private-cidrs)):
+If you need to allow access to additional internal networks via the proxy, use the Allowlist CIDRs option ([`CODER_AI_GATEWAY_PROXY_ALLOWED_PRIVATE_CIDRS`](../../../reference/cli/server/index.md#--ai-gateway-proxy-allowed-private-cidrs)):
 
 ```sh
 CODER_AI_GATEWAY_PROXY_ALLOWED_PRIVATE_CIDRS=10.0.0.0/8,172.16.0.0/12
@@ -256,7 +256,7 @@ If your organization requires all outbound traffic to pass through a corporate p
 
 ### How it works
 
-Tunneled requests (non-allowlisted domains) are forwarded to the upstream proxy configured via [`CODER_AI_GATEWAY_PROXY_UPSTREAM`](../../../reference/cli/server.md#--ai-gateway-proxy-upstream).
+Tunneled requests (non-allowlisted domains) are forwarded to the upstream proxy configured via [`CODER_AI_GATEWAY_PROXY_UPSTREAM`](../../../reference/cli/server/index.md#--ai-gateway-proxy-upstream).
 
 MITM'd requests (AI provider domains) are forwarded to AI Gateway, which then communicates with AI providers.
 To ensure AI Gateway also routes requests through the upstream proxy, make sure to configure the proxy settings for the `coderd` process.
@@ -283,7 +283,7 @@ CODER_AI_GATEWAY_PROXY_UPSTREAM=https://<corporate-proxy-url>:8080
 CODER_AI_GATEWAY_PROXY_UPSTREAM_CA=/path/to/corporate-ca.crt
 ```
 
-If the system already trusts the upstream proxy's CA certificate, [`CODER_AI_GATEWAY_PROXY_UPSTREAM_CA`](../../../reference/cli/server.md#--ai-gateway-proxy-upstream-ca) is not required.
+If the system already trusts the upstream proxy's CA certificate, [`CODER_AI_GATEWAY_PROXY_UPSTREAM_CA`](../../../reference/cli/server/index.md#--ai-gateway-proxy-upstream-ca) is not required.
 
 ## Client Configuration
 
diff --git a/docs/ai-coder/ai-gateway/auth.md b/docs/ai-coder/ai-gateway/auth.md
index afeed229c2..aa857ca8ce 100644
--- a/docs/ai-coder/ai-gateway/auth.md
+++ b/docs/ai-coder/ai-gateway/auth.md
@@ -36,7 +36,7 @@ From the dashboard, go to **Account settings** > **Tokens** and create a new tok
 For long-lived tokens, refer to [Sessions and API tokens](../../admin/users/sessions-tokens.md#generate-a-long-lived-api-token-on-behalf-of-yourself).
 For headless or service-account use, refer to [Headless authentication](../../admin/users/headless-auth.md).
 
-From the CLI, print your current session token with [`coder login token`](../../reference/cli/login_token.md):
+From the CLI, print your current session token with [`coder login token`](../../reference/cli/login/token.md):
 
 ```sh
 coder login token
@@ -52,7 +52,7 @@ Use short lifetimes for automation and CI to limit the blast radius if a token l
 
 ### Retrieve your session token
 
-If you're logged in with the Coder CLI, retrieve your current session token with [`coder login token`](../../reference/cli/login_token.md):
+If you're logged in with the Coder CLI, retrieve your current session token with [`coder login token`](../../reference/cli/login/token.md):
 
 ```sh
 export ANTHROPIC_API_KEY=$(coder login token)
@@ -112,7 +112,7 @@ A replica records a heartbeat when its control connection is established, then r
 The heartbeat reports control-connection liveness rather than client request volume.
 Coder stores one timestamp per key, so replicas that share a key cannot be distinguished.
 
-For usage and flags, refer to the generated CLI reference for [creating](../../reference/cli/ai-gateway_keys_create.md), [listing](../../reference/cli/ai-gateway_keys_list.md), and [deleting](../../reference/cli/ai-gateway_keys_delete.md) gateway keys.
+For usage and flags, refer to the generated CLI reference for [creating](../../reference/cli/ai-gateway/keys/create.md), [listing](../../reference/cli/ai-gateway/keys/list.md), and [deleting](../../reference/cli/ai-gateway/keys/delete.md) gateway keys.
 
 ### Rotate a gateway key
 
diff --git a/docs/ai-coder/ai-gateway/monitoring.md b/docs/ai-coder/ai-gateway/monitoring.md
index 07ff5260b6..807f0b368d 100644
--- a/docs/ai-coder/ai-gateway/monitoring.md
+++ b/docs/ai-coder/ai-gateway/monitoring.md
@@ -183,7 +183,7 @@ The startup probe is disabled by default.
 
 Standalone replicas use the standard Coder logging options.
 Configure them on every replica or through `coder.env` in the AI Gateway Helm chart.
-Refer to the [`coder ai-gateway start` logging options](../../reference/cli/ai-gateway_start.md#-l---log-filter) for configuration details.
+Refer to the [`coder ai-gateway start` logging options](../../reference/cli/ai-gateway/start.md#-l---log-filter) for configuration details.
 
 ### Structured interception logs
 
@@ -262,7 +262,7 @@ The exporter always dials without TLS, so an `https://` endpoint is still contac
 Set only the Honeycomb key to export to Honeycomb alone, or set both to export to Honeycomb and an OTLP collector.
 
 The embedded and standalone gateways support the same tracing configuration options, but each standalone replica must be configured separately.
-Refer to the [`coder server` tracing options](../../reference/cli/server.md#--trace) for the embedded gateway and the [`coder ai-gateway start` tracing options](../../reference/cli/ai-gateway_start.md#--trace) for standalone replicas.
+Refer to the [`coder server` tracing options](../../reference/cli/server/index.md#--trace) for the embedded gateway and the [`coder ai-gateway start` tracing options](../../reference/cli/ai-gateway/start.md#--trace) for standalone replicas.
 Configure tracing on every standalone process or through `coder.env` in the AI Gateway Helm chart.
 
 The following minimal configuration enables tracing and exports spans over OTLP/gRPC:
diff --git a/docs/ai-coder/ai-gateway/setup.md b/docs/ai-coder/ai-gateway/setup.md
index aef4b23ce7..75ce8f6ad2 100644
--- a/docs/ai-coder/ai-gateway/setup.md
+++ b/docs/ai-coder/ai-gateway/setup.md
@@ -141,8 +141,8 @@ ai_gateway:
 
 These logs are written to the same output stream as all other `coderd` logs,
 using the format configured by
-[`--log-human`](../../reference/cli/server.md#--log-human) (default, writes to
-stderr) or [`--log-json`](../../reference/cli/server.md#--log-json). For machine
+[`--log-human`](../../reference/cli/server/index.md#--log-human) (default, writes to
+stderr) or [`--log-json`](../../reference/cli/server/index.md#--log-json). For machine
 ingestion, set `--log-json` to a file path or `/dev/stderr` so that records are
 emitted as JSON.
 
diff --git a/docs/ai-coder/ai-gateway/standalone.md b/docs/ai-coder/ai-gateway/standalone.md
index 0b544564c0..bf5e53f621 100644
--- a/docs/ai-coder/ai-gateway/standalone.md
+++ b/docs/ai-coder/ai-gateway/standalone.md
@@ -63,7 +63,7 @@ Configure at least one [AI provider](./providers.md) in Coder before sending pro
 
 The listener uses HTTP by default.
 Set both `CODER_AI_GATEWAY_TLS_CERT_FILE` and `CODER_AI_GATEWAY_TLS_KEY_FILE` to terminate TLS in the process.
-For all command options, refer to [`coder ai-gateway start`](../../reference/cli/ai-gateway_start.md).
+For all command options, refer to [`coder ai-gateway start`](../../reference/cli/ai-gateway/start.md).
 
 ## Run AI Gateway in Kubernetes
 
diff --git a/docs/ai-coder/mcp-server.md b/docs/ai-coder/mcp-server.md
index bebb49d3e1..5521562712 100644
--- a/docs/ai-coder/mcp-server.md
+++ b/docs/ai-coder/mcp-server.md
@@ -115,7 +115,7 @@ CODER_EXPERIMENTS=mcp-server-http
 ```
 
 For the YAML and Helm forms of the provider setting, refer to [Enable OAuth2 Provider](../admin/integrations/oauth2-provider/index.md#enable-oauth2-provider).
-That page does not cover the experiment; set it with the top-level [`experiments`](../reference/cli/server.md#--experiments) YAML key.
+That page does not cover the experiment; set it with the top-level [`experiments`](../reference/cli/server/index.md#--experiments) YAML key.
 
 ### MCP Registry
 
diff --git a/docs/install/operate/provisioners/index.md b/docs/install/operate/provisioners/index.md
index ccfda66431..b4fd81e2ba 100644
--- a/docs/install/operate/provisioners/index.md
+++ b/docs/install/operate/provisioners/index.md
@@ -3,7 +3,7 @@ title: External provisioners
 ---
 
 By default, the control plane runs
-[built-in provisioner daemons](../../../reference/cli/server.md#--provisioner-daemons),
+[built-in provisioner daemons](../../../reference/cli/server/index.md#--provisioner-daemons),
 which execute `terraform` during workspace and template builds. However, there
 are often benefits to running external provisioner daemons:
 
@@ -30,7 +30,7 @@ For example, running 30 provisioner containers will allow 30 users to start
 workspaces at the same time.
 
 Provisioners are started with the
-[`coder provisioner start`](../../../reference/cli/provisioner_start.md) command in
+[`coder provisioner start`](../../../reference/cli/provisioner/start.md) command in
 the [full Coder binary](https://github.com/coder/coder/releases). Keep reading
 to learn how to start provisioners via Docker, Kubernetes, Systemd, etc.
 
@@ -114,7 +114,7 @@ Global pre-shared keys (PSK) make it difficult to rotate keys or isolate provisi
 
 A deployment-wide PSK can be used to authenticate any provisioner. To use a
 global PSK, set a
-[provisioner daemon pre-shared key (PSK)](../../../reference/cli/server.md#--provisioner-daemon-psk)
+[provisioner daemon pre-shared key (PSK)](../../../reference/cli/server/index.md#--provisioner-daemon-psk)
 on the control plane.
 
 Next, start the provisioner:
@@ -241,17 +241,17 @@ This is illustrated in the below table:
 
 Provisioners can broadly be categorized by scope: `organization` or `user`. The
 scope of a provisioner can be specified with
-[`-tag=scope=<scope>`](../../../reference/cli/provisioner_start.md#-t---tag) when
+[`-tag=scope=<scope>`](../../../reference/cli/provisioner/start.md#-t---tag) when
 starting the provisioner daemon. Only users with at least the
 [Template Admin](../../../admin/users/index.md#roles) role or higher may create
 organization-scoped provisioner daemons.
 
 There are two exceptions:
 
-- [Built-in provisioners](../../../reference/cli/server.md#--provisioner-daemons) are
+- [Built-in provisioners](../../../reference/cli/server/index.md#--provisioner-daemons) are
   always organization-scoped.
 - External provisioners started using a
-  [pre-shared key (PSK)](../../../reference/cli/provisioner_start.md#--psk) are always
+  [pre-shared key (PSK)](../../../reference/cli/provisioner/start.md#--psk) are always
   organization-scoped.
 
 ### Organization-Scoped Provisioners
@@ -375,7 +375,7 @@ docker run --rm -it \
 
 As mentioned above, the control plane will run built-in provisioners by default.
 This can be disabled with a server-wide
-[flag or environment variable](../../../reference/cli/server.md#--provisioner-daemons).
+[flag or environment variable](../../../reference/cli/server/index.md#--provisioner-daemons).
 
 ```sh
 coder server --provisioner-daemons=0
diff --git a/docs/install/plan/architecture.md b/docs/install/plan/architecture.md
index b09b112e3f..5097f376f9 100644
--- a/docs/install/plan/architecture.md
+++ b/docs/install/plan/architecture.md
@@ -95,7 +95,7 @@ external PostgreSQL 13+ database for production deployments.
 A managed PostgreSQL database, with daily backups, is recommended:
 
 - For AWS: Amazon RDS for PostgreSQL (preferably using
-  [RDS IAM authentication](../../reference/cli/server.md#--postgres-auth)).
+  [RDS IAM authentication](../../reference/cli/server/index.md#--postgres-auth)).
 - For Azure: Azure Database for PostgreSQL
 - Flexible Server For GCP: Cloud SQL for PostgreSQL
 
diff --git a/docs/install/plan/sizing/index.md b/docs/install/plan/sizing/index.md
index aeb1f8e122..abd923c1e0 100644
--- a/docs/install/plan/sizing/index.md
+++ b/docs/install/plan/sizing/index.md
@@ -389,7 +389,7 @@ could affect workspace users experience once the platform is live.
    and identify the required values for deployment.
 1. Create a `values.yaml` and add it to your version control system.
 1. Determine the necessary environment variables. Here is the
-   [full list of supported server environment variables](../../../reference/cli/server.md).
+   [full list of supported server environment variables](../../../reference/cli/server/index.md).
 1. Follow our documented
    [steps for installing Coder via Helm](../../server/kubernetes/index.md).
 
diff --git a/docs/install/prepare/airgap.md b/docs/install/prepare/airgap.md
index 7ecc08465a..decd8a3008 100644
--- a/docs/install/prepare/airgap.md
+++ b/docs/install/prepare/airgap.md
@@ -6,17 +6,17 @@ All Coder features are supported in air-gapped / behind firewalls / disconnected
 This is a general comparison. Keep reading for a full tutorial running Coder
 air-gapped with Kubernetes or Docker.
 
-|                           | Public deployments                                                                                                                                                                                                                                                 | Air-gapped deployments                                                                                                                                                                                                                                                                                        |
-|---------------------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| Terraform binary          | By default, Coder downloads Terraform binary from [releases.hashicorp.com](https://releases.hashicorp.com)                                                                                                                                                         | Terraform binary must be included in `PATH` for the VM or container image. [Supported versions](../../../provisioner/terraform/install.go#L27-L28)                                                                                                                                                            |
-| Terraform registry        | Coder templates will attempt to download providers from [registry.terraform.io](https://registry.terraform.io) or [custom source addresses](https://developer.hashicorp.com/terraform/language/providers/requirements#source-addresses) specified in each template | [Custom source addresses](https://developer.hashicorp.com/terraform/language/providers/requirements#source-addresses) can be specified in each Coder template, or a custom registry/mirror can be used. More details below                                                                                    |
-| STUN                      | By default, Coder uses Google's public STUN server for direct workspace connections                                                                                                                                                                                | STUN can be safely [disabled](../../reference/cli/server.md#--derp-server-stun-addresses) users can still connect via [relayed connections](../../admin/networking/index.md#-geo-distribution). Alternatively, you can set a [custom DERP server](../../reference/cli/server.md#--derp-server-stun-addresses) |
-| DERP                      | By default, Coder's built-in DERP relay can be used, or [Tailscale's public relays](../../admin/networking/index.md#relayed-connections).                                                                                                                          | By default, Coder's built-in DERP relay can be used, or [custom relays](../../admin/networking/index.md#custom-relays).                                                                                                                                                                                       |
-| PostgreSQL                | If no [PostgreSQL connection URL](../../reference/cli/server.md#--postgres-url) is specified, Coder will download Postgres from [repo1.maven.org](https://repo1.maven.org)                                                                                         | An external database is required, you must specify a [PostgreSQL connection URL](../../reference/cli/server.md#--postgres-url)                                                                                                                                                                                |
-| Telemetry                 | Telemetry is on by default, and [can be disabled](../../reference/cli/server.md#--telemetry)                                                                                                                                                                       | Telemetry [can be disabled](../../reference/cli/server.md#--telemetry)                                                                                                                                                                                                                                        |
-| Update check              | By default, Coder checks for updates from [GitHub releases](https://github.com/coder/coder/releases)                                                                                                                                                               | Update checks [can be disabled](../../reference/cli/server.md#--update-check)                                                                                                                                                                                                                                 |
-| License validation        | License keys are validated locally using cryptographic signatures. No outbound connection to Coder is required                                                                                                                                                     | No changes needed. See [offline license validation](./licensing.md#offline-license-validation)                                                                                                                                                                                                                |
-| AI Governance Usage Count | By default, deployments with [AI Governance](../../ai-coder/ai-governance.md) report usage data                                                                                                                                                                    | [Contact us](https://coder.com/contact) to request a license with usage reporting off.                                                                                                                                                                                                                        |
+|                           | Public deployments                                                                                                                                                                                                                                                 | Air-gapped deployments                                                                                                                                                                                                                                                                                                    |
+|---------------------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| Terraform binary          | By default, Coder downloads Terraform binary from [releases.hashicorp.com](https://releases.hashicorp.com)                                                                                                                                                         | Terraform binary must be included in `PATH` for the VM or container image. [Supported versions](../../../provisioner/terraform/install.go#L27-L28)                                                                                                                                                                        |
+| Terraform registry        | Coder templates will attempt to download providers from [registry.terraform.io](https://registry.terraform.io) or [custom source addresses](https://developer.hashicorp.com/terraform/language/providers/requirements#source-addresses) specified in each template | [Custom source addresses](https://developer.hashicorp.com/terraform/language/providers/requirements#source-addresses) can be specified in each Coder template, or a custom registry/mirror can be used. More details below                                                                                                |
+| STUN                      | By default, Coder uses Google's public STUN server for direct workspace connections                                                                                                                                                                                | STUN can be safely [disabled](../../reference/cli/server/index.md#--derp-server-stun-addresses) users can still connect via [relayed connections](../../admin/networking/index.md#-geo-distribution). Alternatively, you can set a [custom DERP server](../../reference/cli/server/index.md#--derp-server-stun-addresses) |
+| DERP                      | By default, Coder's built-in DERP relay can be used, or [Tailscale's public relays](../../admin/networking/index.md#relayed-connections).                                                                                                                          | By default, Coder's built-in DERP relay can be used, or [custom relays](../../admin/networking/index.md#custom-relays).                                                                                                                                                                                                   |
+| PostgreSQL                | If no [PostgreSQL connection URL](../../reference/cli/server/index.md#--postgres-url) is specified, Coder will download Postgres from [repo1.maven.org](https://repo1.maven.org)                                                                                   | An external database is required, you must specify a [PostgreSQL connection URL](../../reference/cli/server/index.md#--postgres-url)                                                                                                                                                                                      |
+| Telemetry                 | Telemetry is on by default, and [can be disabled](../../reference/cli/server/index.md#--telemetry)                                                                                                                                                                 | Telemetry [can be disabled](../../reference/cli/server/index.md#--telemetry)                                                                                                                                                                                                                                              |
+| Update check              | By default, Coder checks for updates from [GitHub releases](https://github.com/coder/coder/releases)                                                                                                                                                               | Update checks [can be disabled](../../reference/cli/server/index.md#--update-check)                                                                                                                                                                                                                                       |
+| License validation        | License keys are validated locally using cryptographic signatures. No outbound connection to Coder is required                                                                                                                                                     | No changes needed. See [offline license validation](./licensing.md#offline-license-validation)                                                                                                                                                                                                                            |
+| AI Governance Usage Count | By default, deployments with [AI Governance](../../ai-coder/ai-governance.md) report usage data                                                                                                                                                                    | [Contact us](https://coder.com/contact) to request a license with usage reporting off.                                                                                                                                                                                                                                    |
 
 ## Air-gapped container images
 
@@ -229,7 +229,7 @@ server, as demonstrated in the example below:
 3. Extract the file and move its contents to your server folder.
 4. If you are using NodeJS, you can execute the following command:
    `cd docs && npx http-server .`
-5. Set the [CODER_DOCS_URL](../../reference/cli/server.md#--docs-url) environment
+5. Set the [CODER_DOCS_URL](../../reference/cli/server/index.md#--docs-url) environment
    variable to use the URL of your hosted docs. This way, the Coder UI will
    reference the documentation from your specified URL.
 
diff --git a/docs/install/validate/scale-testing.md b/docs/install/validate/scale-testing.md
index 4385eaf315..8badc8fa8d 100644
--- a/docs/install/validate/scale-testing.md
+++ b/docs/install/validate/scale-testing.md
@@ -118,7 +118,7 @@ While the minimum requirements specify 1&nbsp;CPU core and 2&nbsp;GB of memory p
 #### CPU and memory usage
 
 Enabling
-[agent stats collection](../../reference/cli/server.md#--prometheus-collect-agent-stats)
+[agent stats collection](../../reference/cli/server/index.md#--prometheus-collect-agent-stats)
 (optional) may increase memory consumption.
 
 Enabling direct connections between users and workspace agents (apps or SSH
diff --git a/docs/manifest.json b/docs/manifest.json
index 35255044c7..018a7d0c36 100644
--- a/docs/manifest.json
+++ b/docs/manifest.json
@@ -1697,780 +1697,889 @@
 					"icon_path": "./images/icons/terminal.svg",
 					"children": [
 						{
-							"title": "autoupdate",
-							"description": "Toggle auto-update policy for a workspace",
-							"path": "reference/cli/autoupdate.md"
-						},
-						{
-							"title": "agent-firewall",
+							"title": "`agent-firewall`",
 							"description": "Network isolation tool for monitoring and restricting HTTP/HTTPS requests",
 							"path": "reference/cli/agent-firewall.md"
 						},
 						{
-							"title": "coder",
-							"path": "reference/cli/index.md"
+							"title": "`ai-gateway`",
+							"description": "Manage AI Gateway",
+							"path": "reference/cli/ai-gateway/index.md",
+							"children": [
+								{
+									"title": "`keys`",
+									"description": "Manage AI Gateway keys",
+									"path": "reference/cli/ai-gateway/keys/index.md",
+									"children": [
+										{
+											"title": "`create`",
+											"description": "Create an AI Gateway key",
+											"path": "reference/cli/ai-gateway/keys/create.md"
+										},
+										{
+											"title": "`delete`",
+											"description": "Delete an AI Gateway key",
+											"path": "reference/cli/ai-gateway/keys/delete.md"
+										},
+										{
+											"title": "`list`",
+											"description": "List AI Gateway keys",
+											"path": "reference/cli/ai-gateway/keys/list.md"
+										}
+									]
+								},
+								{
+									"title": "`start`",
+									"description": "Run a standalone AI Gateway server",
+									"path": "reference/cli/ai-gateway/start.md"
+								}
+							]
 						},
 						{
-							"title": "completion",
+							"title": "`autoupdate`",
+							"description": "Toggle auto-update policy for a workspace",
+							"path": "reference/cli/autoupdate.md"
+						},
+						{
+							"title": "`completion`",
 							"description": "Install or update shell completion scripts for the detected or chosen shell.",
 							"path": "reference/cli/completion.md"
 						},
 						{
-							"title": "config-ssh",
+							"title": "`config-ssh`",
 							"description": "Add an SSH Host entry for your workspaces \"ssh workspace.coder\"",
 							"path": "reference/cli/config-ssh.md"
 						},
 						{
-							"title": "create",
+							"title": "`create`",
 							"description": "Create a workspace",
 							"path": "reference/cli/create.md"
 						},
 						{
-							"title": "delete",
+							"title": "`delete`",
 							"description": "Delete a workspace",
 							"path": "reference/cli/delete.md"
 						},
 						{
-							"title": "dotfiles",
+							"title": "`dotfiles`",
 							"description": "Personalize your workspace by applying a canonical dotfiles repository",
 							"path": "reference/cli/dotfiles.md"
 						},
 						{
-							"title": "external-auth",
+							"title": "`external-auth`",
 							"description": "Manage external authentication",
-							"path": "reference/cli/external-auth.md"
+							"path": "reference/cli/external-auth/index.md",
+							"children": [
+								{
+									"title": "`access-token`",
+									"description": "Print auth for an external provider",
+									"path": "reference/cli/external-auth/access-token.md"
+								}
+							]
 						},
 						{
-							"title": "external-auth access-token",
-							"description": "Print auth for an external provider",
-							"path": "reference/cli/external-auth_access-token.md"
-						},
-						{
-							"title": "external-workspaces",
+							"title": "`external-workspaces`",
 							"description": "Create or manage external workspaces",
-							"path": "reference/cli/external-workspaces.md"
+							"path": "reference/cli/external-workspaces/index.md",
+							"children": [
+								{
+									"title": "`agent-instructions`",
+									"description": "Get the instructions for an external agent",
+									"path": "reference/cli/external-workspaces/agent-instructions.md"
+								},
+								{
+									"title": "`create`",
+									"description": "Create a new external workspace",
+									"path": "reference/cli/external-workspaces/create.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List external workspaces",
+									"path": "reference/cli/external-workspaces/list.md"
+								}
+							]
 						},
 						{
-							"title": "external-workspaces agent-instructions",
-							"description": "Get the instructions for an external agent",
-							"path": "reference/cli/external-workspaces_agent-instructions.md"
-						},
-						{
-							"title": "external-workspaces create",
-							"description": "Create a new external workspace",
-							"path": "reference/cli/external-workspaces_create.md"
-						},
-						{
-							"title": "external-workspaces list",
-							"description": "List external workspaces",
-							"path": "reference/cli/external-workspaces_list.md"
-						},
-						{
-							"title": "favorite",
+							"title": "`favorite`",
 							"description": "Add a workspace to your favorites",
 							"path": "reference/cli/favorite.md"
 						},
 						{
-							"title": "features",
+							"title": "`features`",
 							"description": "List Enterprise features",
-							"path": "reference/cli/features.md"
+							"path": "reference/cli/features/index.md",
+							"children": [
+								{
+									"title": "`list`",
+									"path": "reference/cli/features/list.md"
+								}
+							]
 						},
 						{
-							"title": "features list",
-							"path": "reference/cli/features_list.md"
-						},
-						{
-							"title": "groups",
+							"title": "`groups`",
 							"description": "Manage groups",
-							"path": "reference/cli/groups.md"
+							"path": "reference/cli/groups/index.md",
+							"children": [
+								{
+									"title": "`create`",
+									"description": "Create a user group",
+									"path": "reference/cli/groups/create.md"
+								},
+								{
+									"title": "`delete`",
+									"description": "Delete a user group",
+									"path": "reference/cli/groups/delete.md"
+								},
+								{
+									"title": "`edit`",
+									"description": "Edit a user group",
+									"path": "reference/cli/groups/edit.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List user groups",
+									"path": "reference/cli/groups/list.md"
+								}
+							]
 						},
 						{
-							"title": "groups create",
-							"description": "Create a user group",
-							"path": "reference/cli/groups_create.md"
-						},
-						{
-							"title": "groups delete",
-							"description": "Delete a user group",
-							"path": "reference/cli/groups_delete.md"
-						},
-						{
-							"title": "groups edit",
-							"description": "Edit a user group",
-							"path": "reference/cli/groups_edit.md"
-						},
-						{
-							"title": "groups list",
-							"description": "List user groups",
-							"path": "reference/cli/groups_list.md"
-						},
-						{
-							"title": "licenses",
+							"title": "`licenses`",
 							"description": "Add, delete, and list licenses",
-							"path": "reference/cli/licenses.md"
+							"path": "reference/cli/licenses/index.md",
+							"children": [
+								{
+									"title": "`add`",
+									"description": "Add license to Coder deployment",
+									"path": "reference/cli/licenses/add.md"
+								},
+								{
+									"title": "`delete`",
+									"description": "Delete license by ID",
+									"path": "reference/cli/licenses/delete.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List licenses (including expired)",
+									"path": "reference/cli/licenses/list.md"
+								}
+							]
 						},
 						{
-							"title": "licenses add",
-							"description": "Add license to Coder deployment",
-							"path": "reference/cli/licenses_add.md"
-						},
-						{
-							"title": "licenses delete",
-							"description": "Delete license by ID",
-							"path": "reference/cli/licenses_delete.md"
-						},
-						{
-							"title": "licenses list",
-							"description": "List licenses (including expired)",
-							"path": "reference/cli/licenses_list.md"
-						},
-						{
-							"title": "list",
+							"title": "`list`",
 							"description": "List workspaces",
 							"path": "reference/cli/list.md"
 						},
 						{
-							"title": "login",
+							"title": "`login`",
 							"description": "Authenticate with Coder deployment",
-							"path": "reference/cli/login.md"
+							"path": "reference/cli/login/index.md",
+							"children": [
+								{
+									"title": "`token`",
+									"description": "Print the current session token",
+									"path": "reference/cli/login/token.md"
+								}
+							]
 						},
 						{
-							"title": "login token",
-							"description": "Print the current session token",
-							"path": "reference/cli/login_token.md"
-						},
-						{
-							"title": "logout",
+							"title": "`logout`",
 							"description": "Unauthenticate your local session",
 							"path": "reference/cli/logout.md"
 						},
 						{
-							"title": "logs",
+							"title": "`logs`",
 							"description": "View logs for a workspace",
 							"path": "reference/cli/logs.md"
 						},
 						{
-							"title": "netcheck",
+							"title": "`netcheck`",
 							"description": "Print network debug information for DERP and STUN",
 							"path": "reference/cli/netcheck.md"
 						},
 						{
-							"title": "notifications",
+							"title": "`notifications`",
 							"description": "Manage Coder notifications",
-							"path": "reference/cli/notifications.md"
+							"path": "reference/cli/notifications/index.md",
+							"children": [
+								{
+									"title": "`custom`",
+									"description": "Send a custom notification",
+									"path": "reference/cli/notifications/custom.md"
+								},
+								{
+									"title": "`pause`",
+									"description": "Pause notifications",
+									"path": "reference/cli/notifications/pause.md"
+								},
+								{
+									"title": "`resume`",
+									"description": "Resume notifications",
+									"path": "reference/cli/notifications/resume.md"
+								},
+								{
+									"title": "`test`",
+									"description": "Send a test notification",
+									"path": "reference/cli/notifications/test.md"
+								}
+							]
 						},
 						{
-							"title": "notifications custom",
-							"description": "Send a custom notification",
-							"path": "reference/cli/notifications_custom.md"
-						},
-						{
-							"title": "notifications pause",
-							"description": "Pause notifications",
-							"path": "reference/cli/notifications_pause.md"
-						},
-						{
-							"title": "notifications resume",
-							"description": "Resume notifications",
-							"path": "reference/cli/notifications_resume.md"
-						},
-						{
-							"title": "notifications test",
-							"description": "Send a test notification",
-							"path": "reference/cli/notifications_test.md"
-						},
-						{
-							"title": "oauth2-provider",
+							"title": "`oauth2-provider`",
 							"description": "Manage Coder OAuth2 provider settings",
-							"path": "reference/cli/oauth2-provider.md"
+							"path": "reference/cli/oauth2-provider/index.md",
+							"children": [
+								{
+									"title": "`dcr`",
+									"description": "Manage OAuth2 dynamic client registration (RFC 7591)",
+									"path": "reference/cli/oauth2-provider/dcr/index.md",
+									"children": [
+										{
+											"title": "`disable`",
+											"description": "Disable OAuth2 dynamic client registration",
+											"path": "reference/cli/oauth2-provider/dcr/disable.md"
+										},
+										{
+											"title": "`enable`",
+											"description": "Enable OAuth2 dynamic client registration",
+											"path": "reference/cli/oauth2-provider/dcr/enable.md"
+										}
+									]
+								}
+							]
 						},
 						{
-							"title": "oauth2-provider dcr",
-							"description": "Manage OAuth2 dynamic client registration (RFC 7591)",
-							"path": "reference/cli/oauth2-provider_dcr.md"
-						},
-						{
-							"title": "oauth2-provider dcr enable",
-							"description": "Enable OAuth2 dynamic client registration",
-							"path": "reference/cli/oauth2-provider_dcr_enable.md"
-						},
-						{
-							"title": "oauth2-provider dcr disable",
-							"description": "Disable OAuth2 dynamic client registration",
-							"path": "reference/cli/oauth2-provider_dcr_disable.md"
-						},
-						{
-							"title": "open",
+							"title": "`open`",
 							"description": "Open a workspace",
-							"path": "reference/cli/open.md"
+							"path": "reference/cli/open/index.md",
+							"children": [
+								{
+									"title": "`app`",
+									"description": "Open a workspace application.",
+									"path": "reference/cli/open/app.md"
+								},
+								{
+									"title": "`vscode`",
+									"description": "Open a workspace in VS Code Desktop",
+									"path": "reference/cli/open/vscode.md"
+								}
+							]
 						},
 						{
-							"title": "open app",
-							"description": "Open a workspace application.",
-							"path": "reference/cli/open_app.md"
-						},
-						{
-							"title": "open vscode",
-							"description": "Open a workspace in VS Code Desktop",
-							"path": "reference/cli/open_vscode.md"
-						},
-						{
-							"title": "organizations",
+							"title": "`organizations`",
 							"description": "Organization related commands",
-							"path": "reference/cli/organizations.md"
+							"path": "reference/cli/organizations/index.md",
+							"children": [
+								{
+									"title": "`create`",
+									"description": "Create a new organization.",
+									"path": "reference/cli/organizations/create.md"
+								},
+								{
+									"title": "`delete`",
+									"description": "Delete an organization",
+									"path": "reference/cli/organizations/delete.md"
+								},
+								{
+									"title": "`edit`",
+									"description": "Edit organization settings.",
+									"path": "reference/cli/organizations/edit.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List all organizations",
+									"path": "reference/cli/organizations/list.md"
+								},
+								{
+									"title": "`members`",
+									"description": "Manage organization members",
+									"path": "reference/cli/organizations/members/index.md",
+									"children": [
+										{
+											"title": "`add`",
+											"description": "Add a new member to the current organization",
+											"path": "reference/cli/organizations/members/add.md"
+										},
+										{
+											"title": "`edit-roles`",
+											"description": "Edit organization member's roles",
+											"path": "reference/cli/organizations/members/edit-roles.md"
+										},
+										{
+											"title": "`list`",
+											"description": "List all organization members",
+											"path": "reference/cli/organizations/members/list.md"
+										},
+										{
+											"title": "`remove`",
+											"description": "Remove a new member to the current organization",
+											"path": "reference/cli/organizations/members/remove.md"
+										}
+									]
+								},
+								{
+									"title": "`roles`",
+									"description": "Manage organization roles.",
+									"path": "reference/cli/organizations/roles/index.md",
+									"children": [
+										{
+											"title": "`create`",
+											"description": "Create a new organization custom role",
+											"path": "reference/cli/organizations/roles/create.md"
+										},
+										{
+											"title": "`show`",
+											"description": "Show role(s)",
+											"path": "reference/cli/organizations/roles/show.md"
+										},
+										{
+											"title": "`update`",
+											"description": "Update an organization custom role",
+											"path": "reference/cli/organizations/roles/update.md"
+										}
+									]
+								},
+								{
+									"title": "`settings`",
+									"description": "Manage organization settings.",
+									"path": "reference/cli/organizations/settings/index.md",
+									"children": [
+										{
+											"title": "`set`",
+											"description": "Update specified organization setting.",
+											"path": "reference/cli/organizations/settings/set/index.md",
+											"children": [
+												{
+													"title": "`group-sync`",
+													"description": "Group sync settings to sync groups from an IdP.",
+													"path": "reference/cli/organizations/settings/set/group-sync.md"
+												},
+												{
+													"title": "`organization-sync`",
+													"description": "Organization sync settings to sync organization memberships from an IdP.",
+													"path": "reference/cli/organizations/settings/set/organization-sync.md"
+												},
+												{
+													"title": "`role-sync`",
+													"description": "Role sync settings to sync organization roles from an IdP.",
+													"path": "reference/cli/organizations/settings/set/role-sync.md"
+												},
+												{
+													"title": "`workspace-sharing`",
+													"description": "Workspace sharing settings for the organization.",
+													"path": "reference/cli/organizations/settings/set/workspace-sharing.md"
+												}
+											]
+										},
+										{
+											"title": "`show`",
+											"description": "Outputs specified organization setting.",
+											"path": "reference/cli/organizations/settings/show/index.md",
+											"children": [
+												{
+													"title": "`group-sync`",
+													"description": "Group sync settings to sync groups from an IdP.",
+													"path": "reference/cli/organizations/settings/show/group-sync.md"
+												},
+												{
+													"title": "`organization-sync`",
+													"description": "Organization sync settings to sync organization memberships from an IdP.",
+													"path": "reference/cli/organizations/settings/show/organization-sync.md"
+												},
+												{
+													"title": "`role-sync`",
+													"description": "Role sync settings to sync organization roles from an IdP.",
+													"path": "reference/cli/organizations/settings/show/role-sync.md"
+												},
+												{
+													"title": "`workspace-sharing`",
+													"description": "Workspace sharing settings for the organization.",
+													"path": "reference/cli/organizations/settings/show/workspace-sharing.md"
+												}
+											]
+										}
+									]
+								},
+								{
+									"title": "`show`",
+									"description": "Show the organization. Using \"selected\" will show the selected organization from the \"--org\" flag. Using \"me\" will show all organizations you are a member of.",
+									"path": "reference/cli/organizations/show.md"
+								}
+							]
 						},
 						{
-							"title": "organizations create",
-							"description": "Create a new organization.",
-							"path": "reference/cli/organizations_create.md"
-						},
-						{
-							"title": "organizations delete",
-							"description": "Delete an organization",
-							"path": "reference/cli/organizations_delete.md"
-						},
-						{
-							"title": "organizations edit",
-							"description": "Edit an organization.",
-							"path": "reference/cli/organizations_edit.md"
-						},
-						{
-							"title": "organizations list",
-							"description": "List all organizations",
-							"path": "reference/cli/organizations_list.md"
-						},
-						{
-							"title": "organizations members",
-							"description": "Manage organization members",
-							"path": "reference/cli/organizations_members.md"
-						},
-						{
-							"title": "organizations members add",
-							"description": "Add a new member to the current organization",
-							"path": "reference/cli/organizations_members_add.md"
-						},
-						{
-							"title": "organizations members edit-roles",
-							"description": "Edit organization member's roles",
-							"path": "reference/cli/organizations_members_edit-roles.md"
-						},
-						{
-							"title": "organizations members list",
-							"description": "List all organization members",
-							"path": "reference/cli/organizations_members_list.md"
-						},
-						{
-							"title": "organizations members remove",
-							"description": "Remove a new member to the current organization",
-							"path": "reference/cli/organizations_members_remove.md"
-						},
-						{
-							"title": "organizations roles",
-							"description": "Manage organization roles.",
-							"path": "reference/cli/organizations_roles.md"
-						},
-						{
-							"title": "organizations roles create",
-							"description": "Create a new organization custom role",
-							"path": "reference/cli/organizations_roles_create.md"
-						},
-						{
-							"title": "organizations roles show",
-							"description": "Show role(s)",
-							"path": "reference/cli/organizations_roles_show.md"
-						},
-						{
-							"title": "organizations roles update",
-							"description": "Update an organization custom role",
-							"path": "reference/cli/organizations_roles_update.md"
-						},
-						{
-							"title": "organizations settings",
-							"description": "Manage organization settings.",
-							"path": "reference/cli/organizations_settings.md"
-						},
-						{
-							"title": "organizations settings set",
-							"description": "Update specified organization setting.",
-							"path": "reference/cli/organizations_settings_set.md"
-						},
-						{
-							"title": "organizations settings set group-sync",
-							"description": "Group sync settings to sync groups from an IdP.",
-							"path": "reference/cli/organizations_settings_set_group-sync.md"
-						},
-						{
-							"title": "organizations settings set organization-sync",
-							"description": "Organization sync settings to sync organization memberships from an IdP.",
-							"path": "reference/cli/organizations_settings_set_organization-sync.md"
-						},
-						{
-							"title": "organizations settings set role-sync",
-							"description": "Role sync settings to sync organization roles from an IdP.",
-							"path": "reference/cli/organizations_settings_set_role-sync.md"
-						},
-						{
-							"title": "organizations settings set workspace-sharing",
-							"description": "Workspace sharing settings for the organization.",
-							"path": "reference/cli/organizations_settings_set_workspace-sharing.md"
-						},
-						{
-							"title": "organizations settings show",
-							"description": "Outputs specified organization setting.",
-							"path": "reference/cli/organizations_settings_show.md"
-						},
-						{
-							"title": "organizations settings show group-sync",
-							"description": "Group sync settings to sync groups from an IdP.",
-							"path": "reference/cli/organizations_settings_show_group-sync.md"
-						},
-						{
-							"title": "organizations settings show organization-sync",
-							"description": "Organization sync settings to sync organization memberships from an IdP.",
-							"path": "reference/cli/organizations_settings_show_organization-sync.md"
-						},
-						{
-							"title": "organizations settings show role-sync",
-							"description": "Role sync settings to sync organization roles from an IdP.",
-							"path": "reference/cli/organizations_settings_show_role-sync.md"
-						},
-						{
-							"title": "organizations settings show workspace-sharing",
-							"description": "Workspace sharing settings for the organization.",
-							"path": "reference/cli/organizations_settings_show_workspace-sharing.md"
-						},
-						{
-							"title": "organizations show",
-							"description": "Show the organization. Using \"selected\" will show the selected organization from the \"--org\" flag. Using \"me\" will show all organizations you are a member of.",
-							"path": "reference/cli/organizations_show.md"
-						},
-						{
-							"title": "ping",
+							"title": "`ping`",
 							"description": "Ping a workspace",
 							"path": "reference/cli/ping.md"
 						},
 						{
-							"title": "port-forward",
+							"title": "`port-forward`",
 							"description": "Forward ports from a workspace to the local machine. For reverse port forwarding, use \"coder ssh -R\".",
 							"path": "reference/cli/port-forward.md"
 						},
 						{
-							"title": "prebuilds",
+							"title": "`prebuilds`",
 							"description": "Manage Coder prebuilds",
-							"path": "reference/cli/prebuilds.md"
+							"path": "reference/cli/prebuilds/index.md",
+							"children": [
+								{
+									"title": "`pause`",
+									"description": "Pause prebuilds",
+									"path": "reference/cli/prebuilds/pause.md"
+								},
+								{
+									"title": "`resume`",
+									"description": "Resume prebuilds",
+									"path": "reference/cli/prebuilds/resume.md"
+								}
+							]
 						},
 						{
-							"title": "prebuilds pause",
-							"description": "Pause prebuilds",
-							"path": "reference/cli/prebuilds_pause.md"
-						},
-						{
-							"title": "prebuilds resume",
-							"description": "Resume prebuilds",
-							"path": "reference/cli/prebuilds_resume.md"
-						},
-						{
-							"title": "provisioner",
+							"title": "`provisioner`",
 							"description": "View and manage provisioner daemons and jobs",
-							"path": "reference/cli/provisioner.md"
+							"path": "reference/cli/provisioner/index.md",
+							"children": [
+								{
+									"title": "`jobs`",
+									"description": "View and manage provisioner jobs",
+									"path": "reference/cli/provisioner/jobs/index.md",
+									"children": [
+										{
+											"title": "`cancel`",
+											"description": "Cancel a provisioner job",
+											"path": "reference/cli/provisioner/jobs/cancel.md"
+										},
+										{
+											"title": "`list`",
+											"description": "List provisioner jobs",
+											"path": "reference/cli/provisioner/jobs/list.md"
+										}
+									]
+								},
+								{
+									"title": "`keys`",
+									"description": "Manage provisioner keys",
+									"path": "reference/cli/provisioner/keys/index.md",
+									"children": [
+										{
+											"title": "`create`",
+											"description": "Create a new provisioner key",
+											"path": "reference/cli/provisioner/keys/create.md"
+										},
+										{
+											"title": "`delete`",
+											"description": "Delete a provisioner key",
+											"path": "reference/cli/provisioner/keys/delete.md"
+										},
+										{
+											"title": "`list`",
+											"description": "List provisioner keys in an organization",
+											"path": "reference/cli/provisioner/keys/list.md"
+										}
+									]
+								},
+								{
+									"title": "`list`",
+									"description": "List provisioner daemons in an organization",
+									"path": "reference/cli/provisioner/list.md"
+								},
+								{
+									"title": "`start`",
+									"description": "Run a provisioner daemon",
+									"path": "reference/cli/provisioner/start.md"
+								}
+							]
 						},
 						{
-							"title": "provisioner jobs",
-							"description": "View and manage provisioner jobs",
-							"path": "reference/cli/provisioner_jobs.md"
-						},
-						{
-							"title": "provisioner jobs cancel",
-							"description": "Cancel a provisioner job",
-							"path": "reference/cli/provisioner_jobs_cancel.md"
-						},
-						{
-							"title": "provisioner jobs list",
-							"description": "List provisioner jobs",
-							"path": "reference/cli/provisioner_jobs_list.md"
-						},
-						{
-							"title": "provisioner keys",
-							"description": "Manage provisioner keys",
-							"path": "reference/cli/provisioner_keys.md"
-						},
-						{
-							"title": "provisioner keys create",
-							"description": "Create a new provisioner key",
-							"path": "reference/cli/provisioner_keys_create.md"
-						},
-						{
-							"title": "provisioner keys delete",
-							"description": "Delete a provisioner key",
-							"path": "reference/cli/provisioner_keys_delete.md"
-						},
-						{
-							"title": "provisioner keys list",
-							"description": "List provisioner keys in an organization",
-							"path": "reference/cli/provisioner_keys_list.md"
-						},
-						{
-							"title": "provisioner list",
-							"description": "List provisioner daemons in an organization",
-							"path": "reference/cli/provisioner_list.md"
-						},
-						{
-							"title": "provisioner start",
-							"description": "Run a provisioner daemon",
-							"path": "reference/cli/provisioner_start.md"
-						},
-						{
-							"title": "publickey",
+							"title": "`publickey`",
 							"description": "Output your Coder public key used for Git operations",
 							"path": "reference/cli/publickey.md"
 						},
 						{
-							"title": "rename",
+							"title": "`rename`",
 							"description": "Rename a workspace",
 							"path": "reference/cli/rename.md"
 						},
 						{
-							"title": "reset-password",
+							"title": "`reset-password`",
 							"description": "Directly connect to the database to reset a user's password",
 							"path": "reference/cli/reset-password.md"
 						},
 						{
-							"title": "restart",
+							"title": "`restart`",
 							"description": "Restart a workspace",
 							"path": "reference/cli/restart.md"
 						},
 						{
-							"title": "schedule",
+							"title": "`schedule`",
 							"description": "Schedule automated start and stop times for workspaces",
-							"path": "reference/cli/schedule.md"
+							"path": "reference/cli/schedule/index.md",
+							"children": [
+								{
+									"title": "`extend`",
+									"description": "Extend the stop time of a currently running workspace instance.",
+									"path": "reference/cli/schedule/extend.md"
+								},
+								{
+									"title": "`show`",
+									"description": "Show workspace schedules",
+									"path": "reference/cli/schedule/show.md"
+								},
+								{
+									"title": "`start`",
+									"description": "Edit workspace start schedule",
+									"path": "reference/cli/schedule/start.md"
+								},
+								{
+									"title": "`stop`",
+									"description": "Edit workspace stop schedule",
+									"path": "reference/cli/schedule/stop.md"
+								}
+							]
 						},
 						{
-							"title": "schedule extend",
-							"description": "Extend the stop time of a currently running workspace instance.",
-							"path": "reference/cli/schedule_extend.md"
-						},
-						{
-							"title": "schedule show",
-							"description": "Show workspace schedules",
-							"path": "reference/cli/schedule_show.md"
-						},
-						{
-							"title": "schedule start",
-							"description": "Edit workspace start schedule",
-							"path": "reference/cli/schedule_start.md"
-						},
-						{
-							"title": "schedule stop",
-							"description": "Edit workspace stop schedule",
-							"path": "reference/cli/schedule_stop.md"
-						},
-						{
-							"title": "secret",
+							"title": "`secret`",
 							"description": "Manage secrets",
-							"path": "reference/cli/secret.md"
+							"path": "reference/cli/secret/index.md",
+							"children": [
+								{
+									"title": "`create`",
+									"description": "Create a secret",
+									"path": "reference/cli/secret/create.md"
+								},
+								{
+									"title": "`delete`",
+									"description": "Delete a secret",
+									"path": "reference/cli/secret/delete.md"
+								},
+								{
+									"title": "`disable`",
+									"description": "Disable a secret without removing it",
+									"path": "reference/cli/secret/disable.md"
+								},
+								{
+									"title": "`enable`",
+									"description": "Enable a secret so it is injected into workspaces",
+									"path": "reference/cli/secret/enable.md"
+								},
+								{
+									"title": "`import`",
+									"description": "Import secrets from a file",
+									"path": "reference/cli/secret/import.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List secrets, or show one by name",
+									"path": "reference/cli/secret/list.md"
+								},
+								{
+									"title": "`update`",
+									"description": "Update a secret",
+									"path": "reference/cli/secret/update.md"
+								}
+							]
 						},
 						{
-							"title": "secret create",
-							"description": "Create a secret",
-							"path": "reference/cli/secret_create.md"
-						},
-						{
-							"title": "secret update",
-							"description": "Update a secret",
-							"path": "reference/cli/secret_update.md"
-						},
-						{
-							"title": "secret import",
-							"description": "Import secrets from a file",
-							"path": "reference/cli/secret_import.md"
-						},
-						{
-							"title": "secret list",
-							"description": "List secrets, or show one by name",
-							"path": "reference/cli/secret_list.md"
-						},
-						{
-							"title": "secret delete",
-							"description": "Delete a secret",
-							"path": "reference/cli/secret_delete.md"
-						},
-						{
-							"title": "server",
+							"title": "`server`",
 							"description": "Start a Coder server",
-							"path": "reference/cli/server.md"
+							"path": "reference/cli/server/index.md",
+							"children": [
+								{
+									"title": "`create-admin-user`",
+									"description": "Create a new admin user with the given username, email and password and adds it to every organization.",
+									"path": "reference/cli/server/create-admin-user.md"
+								},
+								{
+									"title": "`dbcrypt`",
+									"description": "Manage database encryption.",
+									"path": "reference/cli/server/dbcrypt/index.md",
+									"children": [
+										{
+											"title": "`decrypt`",
+											"description": "Decrypt a previously encrypted database.",
+											"path": "reference/cli/server/dbcrypt/decrypt.md"
+										},
+										{
+											"title": "`delete`",
+											"description": "Delete all encrypted data from the database. THIS IS A DESTRUCTIVE OPERATION.",
+											"path": "reference/cli/server/dbcrypt/delete.md"
+										},
+										{
+											"title": "`rotate`",
+											"description": "Rotate database encryption keys.",
+											"path": "reference/cli/server/dbcrypt/rotate.md"
+										}
+									]
+								},
+								{
+									"title": "`fix-oidc-links`",
+									"description": "Reset OIDC linked IDs that do not match the expected issuer, allowing users to re-authenticate.",
+									"path": "reference/cli/server/fix-oidc-links.md"
+								},
+								{
+									"title": "`postgres-builtin-serve`",
+									"description": "Run the built-in PostgreSQL deployment.",
+									"path": "reference/cli/server/postgres-builtin-serve.md"
+								},
+								{
+									"title": "`postgres-builtin-url`",
+									"description": "Output the connection URL for the built-in PostgreSQL deployment.",
+									"path": "reference/cli/server/postgres-builtin-url.md"
+								}
+							]
 						},
 						{
-							"title": "server create-admin-user",
-							"description": "Create a new admin user with the given username, email and password and adds it to every organization.",
-							"path": "reference/cli/server_create-admin-user.md"
-						},
-						{
-							"title": "server dbcrypt",
-							"description": "Manage database encryption.",
-							"path": "reference/cli/server_dbcrypt.md"
-						},
-						{
-							"title": "server dbcrypt decrypt",
-							"description": "Decrypt a previously encrypted database.",
-							"path": "reference/cli/server_dbcrypt_decrypt.md"
-						},
-						{
-							"title": "server dbcrypt delete",
-							"description": "Delete all encrypted data from the database. THIS IS A DESTRUCTIVE OPERATION.",
-							"path": "reference/cli/server_dbcrypt_delete.md"
-						},
-						{
-							"title": "server dbcrypt rotate",
-							"description": "Rotate database encryption keys.",
-							"path": "reference/cli/server_dbcrypt_rotate.md"
-						},
-						{
-							"title": "server postgres-builtin-serve",
-							"description": "Run the built-in PostgreSQL deployment.",
-							"path": "reference/cli/server_postgres-builtin-serve.md"
-						},
-						{
-							"title": "server postgres-builtin-url",
-							"description": "Output the connection URL for the built-in PostgreSQL deployment.",
-							"path": "reference/cli/server_postgres-builtin-url.md"
-						},
-						{
-							"title": "show",
+							"title": "`show`",
 							"description": "Display details of a workspace's resources and agents",
 							"path": "reference/cli/show.md"
 						},
 						{
-							"title": "speedtest",
+							"title": "`speedtest`",
 							"description": "Run upload and download tests from your machine to a workspace",
 							"path": "reference/cli/speedtest.md"
 						},
 						{
-							"title": "ssh",
+							"title": "`ssh`",
 							"description": "Start a shell into a workspace or run a command",
 							"path": "reference/cli/ssh.md"
 						},
 						{
-							"title": "start",
+							"title": "`start`",
 							"description": "Start a workspace",
 							"path": "reference/cli/start.md"
 						},
 						{
-							"title": "stat",
+							"title": "`stat`",
 							"description": "Show resource usage for the current workspace.",
-							"path": "reference/cli/stat.md"
+							"path": "reference/cli/stat/index.md",
+							"children": [
+								{
+									"title": "`cpu`",
+									"description": "Show CPU usage, in cores.",
+									"path": "reference/cli/stat/cpu.md"
+								},
+								{
+									"title": "`disk`",
+									"description": "Show disk usage, in gigabytes.",
+									"path": "reference/cli/stat/disk.md"
+								},
+								{
+									"title": "`mem`",
+									"description": "Show memory usage, in gigabytes.",
+									"path": "reference/cli/stat/mem.md"
+								}
+							]
 						},
 						{
-							"title": "stat cpu",
-							"description": "Show CPU usage, in cores.",
-							"path": "reference/cli/stat_cpu.md"
-						},
-						{
-							"title": "stat disk",
-							"description": "Show disk usage, in gigabytes.",
-							"path": "reference/cli/stat_disk.md"
-						},
-						{
-							"title": "stat mem",
-							"description": "Show memory usage, in gigabytes.",
-							"path": "reference/cli/stat_mem.md"
-						},
-						{
-							"title": "state",
+							"title": "`state`",
 							"description": "Manually manage Terraform state to fix broken workspaces",
-							"path": "reference/cli/state.md"
+							"path": "reference/cli/state/index.md",
+							"children": [
+								{
+									"title": "`pull`",
+									"description": "Pull a Terraform state file from a workspace.",
+									"path": "reference/cli/state/pull.md"
+								},
+								{
+									"title": "`push`",
+									"description": "Push a Terraform state file to a workspace.",
+									"path": "reference/cli/state/push.md"
+								}
+							]
 						},
 						{
-							"title": "state pull",
-							"description": "Pull a Terraform state file from a workspace.",
-							"path": "reference/cli/state_pull.md"
-						},
-						{
-							"title": "state push",
-							"description": "Push a Terraform state file to a workspace.",
-							"path": "reference/cli/state_push.md"
-						},
-						{
-							"title": "stop",
+							"title": "`stop`",
 							"description": "Stop a workspace",
 							"path": "reference/cli/stop.md"
 						},
 						{
-							"title": "support",
+							"title": "`support`",
 							"description": "Commands for troubleshooting issues with a Coder deployment.",
-							"path": "reference/cli/support.md"
+							"path": "reference/cli/support/index.md",
+							"children": [
+								{
+									"title": "`bundle`",
+									"description": "Generate a support bundle to troubleshoot issues connecting to a workspace.",
+									"path": "reference/cli/support/bundle.md"
+								}
+							]
 						},
 						{
-							"title": "support bundle",
-							"description": "Generate a support bundle to troubleshoot issues connecting to a workspace.",
-							"path": "reference/cli/support_bundle.md"
-						},
-						{
-							"title": "templates",
+							"title": "`templates`",
 							"description": "Manage templates",
-							"path": "reference/cli/templates.md"
+							"path": "reference/cli/templates/index.md",
+							"children": [
+								{
+									"title": "`archive`",
+									"description": "Archive unused or failed template versions from a given template(s)",
+									"path": "reference/cli/templates/archive.md"
+								},
+								{
+									"title": "`create`",
+									"description": "DEPRECATED: Create a template from the current directory or as specified by flag",
+									"path": "reference/cli/templates/create.md"
+								},
+								{
+									"title": "`delete`",
+									"description": "Delete templates",
+									"path": "reference/cli/templates/delete.md"
+								},
+								{
+									"title": "`edit`",
+									"description": "Edit the metadata of a template by name.",
+									"path": "reference/cli/templates/edit.md"
+								},
+								{
+									"title": "`init`",
+									"description": "Get started with a templated template.",
+									"path": "reference/cli/templates/init.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List all the templates available for the organization",
+									"path": "reference/cli/templates/list.md"
+								},
+								{
+									"title": "`presets`",
+									"description": "Manage presets of the specified template",
+									"path": "reference/cli/templates/presets/index.md",
+									"children": [
+										{
+											"title": "`list`",
+											"description": "List all presets of the specified template. Defaults to the active template version.",
+											"path": "reference/cli/templates/presets/list.md"
+										}
+									]
+								},
+								{
+									"title": "`pull`",
+									"description": "Download the active, latest, or specified version of a template to a path.",
+									"path": "reference/cli/templates/pull.md"
+								},
+								{
+									"title": "`push`",
+									"description": "Create or update a template from the current directory or as specified by flag",
+									"path": "reference/cli/templates/push.md"
+								},
+								{
+									"title": "`versions`",
+									"description": "Manage different versions of the specified template",
+									"path": "reference/cli/templates/versions/index.md",
+									"children": [
+										{
+											"title": "`archive`",
+											"description": "Archive a template version(s).",
+											"path": "reference/cli/templates/versions/archive.md"
+										},
+										{
+											"title": "`list`",
+											"description": "List all the versions of the specified template",
+											"path": "reference/cli/templates/versions/list.md"
+										},
+										{
+											"title": "`promote`",
+											"description": "Promote a template version to active.",
+											"path": "reference/cli/templates/versions/promote.md"
+										},
+										{
+											"title": "`unarchive`",
+											"description": "Unarchive a template version(s).",
+											"path": "reference/cli/templates/versions/unarchive.md"
+										}
+									]
+								}
+							]
 						},
 						{
-							"title": "templates archive",
-							"description": "Archive unused or failed template versions from a given template(s)",
-							"path": "reference/cli/templates_archive.md"
-						},
-						{
-							"title": "templates create",
-							"description": "DEPRECATED: Create a template from the current directory or as specified by flag",
-							"path": "reference/cli/templates_create.md"
-						},
-						{
-							"title": "templates delete",
-							"description": "Delete templates",
-							"path": "reference/cli/templates_delete.md"
-						},
-						{
-							"title": "templates edit",
-							"description": "Edit the metadata of a template by name.",
-							"path": "reference/cli/templates_edit.md"
-						},
-						{
-							"title": "templates init",
-							"description": "Get started with a templated template.",
-							"path": "reference/cli/templates_init.md"
-						},
-						{
-							"title": "templates list",
-							"description": "List all the templates available for the organization",
-							"path": "reference/cli/templates_list.md"
-						},
-						{
-							"title": "templates presets",
-							"description": "Manage presets of the specified template",
-							"path": "reference/cli/templates_presets.md"
-						},
-						{
-							"title": "templates presets list",
-							"description": "List all presets of the specified template. Defaults to the active template version.",
-							"path": "reference/cli/templates_presets_list.md"
-						},
-						{
-							"title": "templates pull",
-							"description": "Download the active, latest, or specified version of a template to a path.",
-							"path": "reference/cli/templates_pull.md"
-						},
-						{
-							"title": "templates push",
-							"description": "Create or update a template from the current directory or as specified by flag",
-							"path": "reference/cli/templates_push.md"
-						},
-						{
-							"title": "templates versions",
-							"description": "Manage different versions of the specified template",
-							"path": "reference/cli/templates_versions.md"
-						},
-						{
-							"title": "templates versions archive",
-							"description": "Archive a template version(s).",
-							"path": "reference/cli/templates_versions_archive.md"
-						},
-						{
-							"title": "templates versions list",
-							"description": "List all the versions of the specified template",
-							"path": "reference/cli/templates_versions_list.md"
-						},
-						{
-							"title": "templates versions promote",
-							"description": "Promote a template version to active.",
-							"path": "reference/cli/templates_versions_promote.md"
-						},
-						{
-							"title": "templates versions unarchive",
-							"description": "Unarchive a template version(s).",
-							"path": "reference/cli/templates_versions_unarchive.md"
-						},
-						{
-							"title": "tokens",
+							"title": "`tokens`",
 							"description": "Manage personal access tokens",
-							"path": "reference/cli/tokens.md"
+							"path": "reference/cli/tokens/index.md",
+							"children": [
+								{
+									"title": "`create`",
+									"description": "Create a token",
+									"path": "reference/cli/tokens/create.md"
+								},
+								{
+									"title": "`list`",
+									"description": "List tokens",
+									"path": "reference/cli/tokens/list.md"
+								},
+								{
+									"title": "`remove`",
+									"description": "Expire or delete a token",
+									"path": "reference/cli/tokens/remove.md"
+								},
+								{
+									"title": "`view`",
+									"description": "Display detailed information about a token",
+									"path": "reference/cli/tokens/view.md"
+								}
+							]
 						},
 						{
-							"title": "tokens create",
-							"description": "Create a token",
-							"path": "reference/cli/tokens_create.md"
-						},
-						{
-							"title": "tokens list",
-							"description": "List tokens",
-							"path": "reference/cli/tokens_list.md"
-						},
-						{
-							"title": "tokens remove",
-							"description": "Expire or delete a token",
-							"path": "reference/cli/tokens_remove.md"
-						},
-						{
-							"title": "tokens view",
-							"description": "Display detailed information about a token",
-							"path": "reference/cli/tokens_view.md"
-						},
-						{
-							"title": "unfavorite",
+							"title": "`unfavorite`",
 							"description": "Remove a workspace from your favorites",
 							"path": "reference/cli/unfavorite.md"
 						},
 						{
-							"title": "update",
+							"title": "`update`",
 							"description": "Will update and start a given workspace if it is out of date. If the workspace is already running, it will be stopped first.",
 							"path": "reference/cli/update.md"
 						},
 						{
-							"title": "users",
+							"title": "`users`",
 							"description": "Manage users",
-							"path": "reference/cli/users.md"
+							"path": "reference/cli/users/index.md",
+							"children": [
+								{
+									"title": "`activate`",
+									"description": "Update a user's status to 'active'. Active users can fully interact with the platform",
+									"path": "reference/cli/users/activate.md"
+								},
+								{
+									"title": "`create`",
+									"description": "Create a new user.",
+									"path": "reference/cli/users/create.md"
+								},
+								{
+									"title": "`delete`",
+									"description": "Delete a user by username or user_id.",
+									"path": "reference/cli/users/delete.md"
+								},
+								{
+									"title": "`edit-roles`",
+									"description": "Edit a user's roles by username or id",
+									"path": "reference/cli/users/edit-roles.md"
+								},
+								{
+									"title": "`list`",
+									"description": "Prints the list of users.",
+									"path": "reference/cli/users/list.md"
+								},
+								{
+									"title": "`oidc-claims`",
+									"description": "Display the OIDC claims for the authenticated user.",
+									"path": "reference/cli/users/oidc-claims.md"
+								},
+								{
+									"title": "`show`",
+									"description": "Show a single user. Use 'me' to indicate the currently authenticated user.",
+									"path": "reference/cli/users/show.md"
+								},
+								{
+									"title": "`suspend`",
+									"description": "Update a user's status to 'suspended'. A suspended user cannot log into the platform",
+									"path": "reference/cli/users/suspend.md"
+								}
+							]
 						},
 						{
-							"title": "users activate",
-							"description": "Update a user's status to 'active'. Active users can fully interact with the platform",
-							"path": "reference/cli/users_activate.md"
-						},
-						{
-							"title": "users create",
-							"description": "Create a new user.",
-							"path": "reference/cli/users_create.md"
-						},
-						{
-							"title": "users delete",
-							"description": "Delete a user by username or user_id.",
-							"path": "reference/cli/users_delete.md"
-						},
-						{
-							"title": "users edit-roles",
-							"description": "Edit a user's roles by username or id",
-							"path": "reference/cli/users_edit-roles.md"
-						},
-						{
-							"title": "users list",
-							"description": "Prints the list of users.",
-							"path": "reference/cli/users_list.md"
-						},
-						{
-							"title": "users oidc-claims",
-							"description": "Display the OIDC claims for the authenticated user.",
-							"path": "reference/cli/users_oidc-claims.md"
-						},
-						{
-							"title": "users show",
-							"description": "Show a single user. Use 'me' to indicate the currently authenticated user.",
-							"path": "reference/cli/users_show.md"
-						},
-						{
-							"title": "users suspend",
-							"description": "Update a user's status to 'suspended'. A suspended user cannot log into the platform",
-							"path": "reference/cli/users_suspend.md"
-						},
-						{
-							"title": "version",
+							"title": "`version`",
 							"description": "Show coder version",
 							"path": "reference/cli/version.md"
 						},
 						{
-							"title": "whoami",
+							"title": "`whoami`",
 							"description": "Fetch authenticated user info for Coder deployment",
 							"path": "reference/cli/whoami.md"
 						}
diff --git a/docs/reference/cli/agent-firewall.md b/docs/reference/cli/agent-firewall.md
index c4e849c072..d1db4e8f7c 100644
--- a/docs/reference/cli/agent-firewall.md
+++ b/docs/reference/cli/agent-firewall.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: agent-firewall
+title: "`coder agent-firewall`"
 description: Network isolation tool for monitoring and restricting HTTP/HTTPS requests
 ---
 
diff --git a/docs/reference/cli/ai-gateway.md b/docs/reference/cli/ai-gateway.md
deleted file mode 100644
index 9becac92f6..0000000000
--- a/docs/reference/cli/ai-gateway.md
+++ /dev/null
@@ -1,22 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: ai-gateway
-description: Manage AI Gateway
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage AI Gateway
-
-## Usage
-
-```console
-coder ai-gateway
-```
-
-## Subcommands
-
-| Name                                        | Purpose                            |
-|---------------------------------------------|------------------------------------|
-| [<code>start</code>](./ai-gateway_start.md) | Run a standalone AI Gateway server |
-| [<code>keys</code>](./ai-gateway_keys.md)   | Manage AI Gateway keys             |
diff --git a/docs/reference/cli/ai-gateway/index.md b/docs/reference/cli/ai-gateway/index.md
new file mode 100644
index 0000000000..1a07b757e7
--- /dev/null
+++ b/docs/reference/cli/ai-gateway/index.md
@@ -0,0 +1,22 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder ai-gateway`"
+description: Manage AI Gateway
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage AI Gateway
+
+## Usage
+
+```console
+coder ai-gateway
+```
+
+## Subcommands
+
+| Name                                 | Purpose                            |
+|--------------------------------------|------------------------------------|
+| [<code>start</code>](./start.md)     | Run a standalone AI Gateway server |
+| [<code>keys</code>](./keys/index.md) | Manage AI Gateway keys             |
diff --git a/docs/reference/cli/ai-gateway_keys_create.md b/docs/reference/cli/ai-gateway/keys/create.md
similarity index 84%
rename from docs/reference/cli/ai-gateway_keys_create.md
rename to docs/reference/cli/ai-gateway/keys/create.md
index 64ce4a0bb1..025264487b 100644
--- a/docs/reference/cli/ai-gateway_keys_create.md
+++ b/docs/reference/cli/ai-gateway/keys/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: ai-gateway keys create
+title: "`coder ai-gateway keys create`"
 description: Create an AI Gateway key
 ---
 
diff --git a/docs/reference/cli/ai-gateway_keys_delete.md b/docs/reference/cli/ai-gateway/keys/delete.md
similarity index 90%
rename from docs/reference/cli/ai-gateway_keys_delete.md
rename to docs/reference/cli/ai-gateway/keys/delete.md
index 753f6c7fe9..91372104a8 100644
--- a/docs/reference/cli/ai-gateway_keys_delete.md
+++ b/docs/reference/cli/ai-gateway/keys/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: ai-gateway keys delete
+title: "`coder ai-gateway keys delete`"
 description: Delete an AI Gateway key
 ---
 
diff --git a/docs/reference/cli/ai-gateway/keys/index.md b/docs/reference/cli/ai-gateway/keys/index.md
new file mode 100644
index 0000000000..64ddde338a
--- /dev/null
+++ b/docs/reference/cli/ai-gateway/keys/index.md
@@ -0,0 +1,23 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder ai-gateway keys`"
+description: Manage AI Gateway keys
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage AI Gateway keys
+
+## Usage
+
+```console
+coder ai-gateway keys
+```
+
+## Subcommands
+
+| Name                               | Purpose                  |
+|------------------------------------|--------------------------|
+| [<code>create</code>](./create.md) | Create an AI Gateway key |
+| [<code>delete</code>](./delete.md) | Delete an AI Gateway key |
+| [<code>list</code>](./list.md)     | List AI Gateway keys     |
diff --git a/docs/reference/cli/ai-gateway_keys_list.md b/docs/reference/cli/ai-gateway/keys/list.md
similarity index 95%
rename from docs/reference/cli/ai-gateway_keys_list.md
rename to docs/reference/cli/ai-gateway/keys/list.md
index 6a8be96d7d..7ec3f8b760 100644
--- a/docs/reference/cli/ai-gateway_keys_list.md
+++ b/docs/reference/cli/ai-gateway/keys/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: ai-gateway keys list
+title: "`coder ai-gateway keys list`"
 description: List AI Gateway keys
 ---
 
diff --git a/docs/reference/cli/ai-gateway_start.md b/docs/reference/cli/ai-gateway/start.md
similarity index 99%
rename from docs/reference/cli/ai-gateway_start.md
rename to docs/reference/cli/ai-gateway/start.md
index a469e0815d..bd3ea1771e 100644
--- a/docs/reference/cli/ai-gateway_start.md
+++ b/docs/reference/cli/ai-gateway/start.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: ai-gateway start
+title: "`coder ai-gateway start`"
 description: Run a standalone AI Gateway server
 ---
 
diff --git a/docs/reference/cli/ai-gateway_keys.md b/docs/reference/cli/ai-gateway_keys.md
deleted file mode 100644
index aee8a20cc2..0000000000
--- a/docs/reference/cli/ai-gateway_keys.md
+++ /dev/null
@@ -1,23 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: ai-gateway keys
-description: Manage AI Gateway keys
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage AI Gateway keys
-
-## Usage
-
-```console
-coder ai-gateway keys
-```
-
-## Subcommands
-
-| Name                                               | Purpose                  |
-|----------------------------------------------------|--------------------------|
-| [<code>create</code>](./ai-gateway_keys_create.md) | Create an AI Gateway key |
-| [<code>delete</code>](./ai-gateway_keys_delete.md) | Delete an AI Gateway key |
-| [<code>list</code>](./ai-gateway_keys_list.md)     | List AI Gateway keys     |
diff --git a/docs/reference/cli/autoupdate.md b/docs/reference/cli/autoupdate.md
index a01df7ddb1..8c6b114eef 100644
--- a/docs/reference/cli/autoupdate.md
+++ b/docs/reference/cli/autoupdate.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: autoupdate
+title: "`coder autoupdate`"
 description: Toggle auto-update policy for a workspace
 ---
 
diff --git a/docs/reference/cli/completion.md b/docs/reference/cli/completion.md
index a0353840b0..0f1fcc3ef7 100644
--- a/docs/reference/cli/completion.md
+++ b/docs/reference/cli/completion.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: completion
+title: "`coder completion`"
 description: Install or update shell completion scripts for the detected or chosen shell.
 ---
 
diff --git a/docs/reference/cli/config-ssh.md b/docs/reference/cli/config-ssh.md
index 1ca8fa5ca3..03f14d2d79 100644
--- a/docs/reference/cli/config-ssh.md
+++ b/docs/reference/cli/config-ssh.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: config-ssh
+title: "`coder config-ssh`"
 description: "Add an SSH Host entry for your workspaces \"ssh workspace.coder\""
 ---
 
diff --git a/docs/reference/cli/create.md b/docs/reference/cli/create.md
index 2130fa9de5..882e7af5cc 100644
--- a/docs/reference/cli/create.md
+++ b/docs/reference/cli/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: create
+title: "`coder create`"
 description: Create a workspace
 ---
 
diff --git a/docs/reference/cli/delete.md b/docs/reference/cli/delete.md
index 3cdb432b41..d84fb35d64 100644
--- a/docs/reference/cli/delete.md
+++ b/docs/reference/cli/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: delete
+title: "`coder delete`"
 description: Delete a workspace
 ---
 
diff --git a/docs/reference/cli/dotfiles.md b/docs/reference/cli/dotfiles.md
index 82b4b99624..a144f65322 100644
--- a/docs/reference/cli/dotfiles.md
+++ b/docs/reference/cli/dotfiles.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: dotfiles
+title: "`coder dotfiles`"
 description: Personalize your workspace by applying a canonical dotfiles repository
 ---
 
diff --git a/docs/reference/cli/external-auth.md b/docs/reference/cli/external-auth.md
deleted file mode 100644
index c93e79f552..0000000000
--- a/docs/reference/cli/external-auth.md
+++ /dev/null
@@ -1,27 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: external-auth
-description: Manage external authentication
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage external authentication
-
-## Usage
-
-```console
-coder external-auth
-```
-
-## Description
-
-```console
-Authenticate with external services inside of a workspace.
-```
-
-## Subcommands
-
-| Name                                                         | Purpose                             |
-|--------------------------------------------------------------|-------------------------------------|
-| [<code>access-token</code>](./external-auth_access-token.md) | Print auth for an external provider |
diff --git a/docs/reference/cli/external-auth_access-token.md b/docs/reference/cli/external-auth/access-token.md
similarity index 98%
rename from docs/reference/cli/external-auth_access-token.md
rename to docs/reference/cli/external-auth/access-token.md
index bf059734ba..7c316ccc77 100644
--- a/docs/reference/cli/external-auth_access-token.md
+++ b/docs/reference/cli/external-auth/access-token.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: external-auth access-token
+title: "`coder external-auth access-token`"
 description: Print auth for an external provider
 ---
 
diff --git a/docs/reference/cli/external-auth/index.md b/docs/reference/cli/external-auth/index.md
new file mode 100644
index 0000000000..13aa457094
--- /dev/null
+++ b/docs/reference/cli/external-auth/index.md
@@ -0,0 +1,27 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder external-auth`"
+description: Manage external authentication
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage external authentication
+
+## Usage
+
+```console
+coder external-auth
+```
+
+## Description
+
+```console
+Authenticate with external services inside of a workspace.
+```
+
+## Subcommands
+
+| Name                                           | Purpose                             |
+|------------------------------------------------|-------------------------------------|
+| [<code>access-token</code>](./access-token.md) | Print auth for an external provider |
diff --git a/docs/reference/cli/external-workspaces.md b/docs/reference/cli/external-workspaces.md
deleted file mode 100644
index 1b8615285e..0000000000
--- a/docs/reference/cli/external-workspaces.md
+++ /dev/null
@@ -1,34 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: external-workspaces
-description: Create or manage external workspaces
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Create or manage external workspaces
-
-## Usage
-
-```console
-coder external-workspaces [flags] [subcommand]
-```
-
-## Subcommands
-
-| Name                                                                           | Purpose                                    |
-|--------------------------------------------------------------------------------|--------------------------------------------|
-| [<code>create</code>](./external-workspaces_create.md)                         | Create a new external workspace            |
-| [<code>agent-instructions</code>](./external-workspaces_agent-instructions.md) | Get the instructions for an external agent |
-| [<code>list</code>](./external-workspaces_list.md)                             | List external workspaces                   |
-
-## Options
-
-### -O, --org
-
-|             |                                  |
-|-------------|----------------------------------|
-| Type        | <code>string</code>              |
-| Environment | <code>$CODER_ORGANIZATION</code> |
-
-Select which organization (uuid or name) to use.
diff --git a/docs/reference/cli/external-workspaces_agent-instructions.md b/docs/reference/cli/external-workspaces/agent-instructions.md
similarity index 89%
rename from docs/reference/cli/external-workspaces_agent-instructions.md
rename to docs/reference/cli/external-workspaces/agent-instructions.md
index 9815ba5563..1cb044986d 100644
--- a/docs/reference/cli/external-workspaces_agent-instructions.md
+++ b/docs/reference/cli/external-workspaces/agent-instructions.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: external-workspaces agent-instructions
+title: "`coder external-workspaces agent-instructions`"
 description: Get the instructions for an external agent
 ---
 
diff --git a/docs/reference/cli/external-workspaces_create.md b/docs/reference/cli/external-workspaces/create.md
similarity index 99%
rename from docs/reference/cli/external-workspaces_create.md
rename to docs/reference/cli/external-workspaces/create.md
index b1d8ddee5e..fbba2d176c 100644
--- a/docs/reference/cli/external-workspaces_create.md
+++ b/docs/reference/cli/external-workspaces/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: external-workspaces create
+title: "`coder external-workspaces create`"
 description: Create a new external workspace
 ---
 
diff --git a/docs/reference/cli/external-workspaces/index.md b/docs/reference/cli/external-workspaces/index.md
new file mode 100644
index 0000000000..08596c4ee9
--- /dev/null
+++ b/docs/reference/cli/external-workspaces/index.md
@@ -0,0 +1,34 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder external-workspaces`"
+description: Create or manage external workspaces
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Create or manage external workspaces
+
+## Usage
+
+```console
+coder external-workspaces [flags] [subcommand]
+```
+
+## Subcommands
+
+| Name                                                       | Purpose                                    |
+|------------------------------------------------------------|--------------------------------------------|
+| [<code>create</code>](./create.md)                         | Create a new external workspace            |
+| [<code>agent-instructions</code>](./agent-instructions.md) | Get the instructions for an external agent |
+| [<code>list</code>](./list.md)                             | List external workspaces                   |
+
+## Options
+
+### -O, --org
+
+|             |                                  |
+|-------------|----------------------------------|
+| Type        | <code>string</code>              |
+| Environment | <code>$CODER_ORGANIZATION</code> |
+
+Select which organization (uuid or name) to use.
diff --git a/docs/reference/cli/external-workspaces_list.md b/docs/reference/cli/external-workspaces/list.md
similarity index 97%
rename from docs/reference/cli/external-workspaces_list.md
rename to docs/reference/cli/external-workspaces/list.md
index d00375f4cb..9815ad902d 100644
--- a/docs/reference/cli/external-workspaces_list.md
+++ b/docs/reference/cli/external-workspaces/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: external-workspaces list
+title: "`coder external-workspaces list`"
 description: List external workspaces
 ---
 
diff --git a/docs/reference/cli/favorite.md b/docs/reference/cli/favorite.md
index 336c134f10..1eab4d2a2c 100644
--- a/docs/reference/cli/favorite.md
+++ b/docs/reference/cli/favorite.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: favorite
+title: "`coder favorite`"
 description: Add a workspace to your favorites
 ---
 
diff --git a/docs/reference/cli/features.md b/docs/reference/cli/features/index.md
similarity index 57%
rename from docs/reference/cli/features.md
rename to docs/reference/cli/features/index.md
index c19291f228..bf87efa5be 100644
--- a/docs/reference/cli/features.md
+++ b/docs/reference/cli/features/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: features
+title: "`coder features`"
 description: List Enterprise features
 ---
 
@@ -20,6 +20,6 @@ coder features
 
 ## Subcommands
 
-| Name                                    | Purpose |
-|-----------------------------------------|---------|
-| [<code>list</code>](./features_list.md) |         |
+| Name                           | Purpose |
+|--------------------------------|---------|
+| [<code>list</code>](./list.md) |         |
diff --git a/docs/reference/cli/features_list.md b/docs/reference/cli/features/list.md
similarity index 95%
rename from docs/reference/cli/features_list.md
rename to docs/reference/cli/features/list.md
index 17cb679177..3773f384b1 100644
--- a/docs/reference/cli/features_list.md
+++ b/docs/reference/cli/features/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: features list
+title: "`coder features list`"
 ---
 
 <!-- DO NOT EDIT | GENERATED CONTENT -->
diff --git a/docs/reference/cli/groups.md b/docs/reference/cli/groups.md
deleted file mode 100644
index c909f6b425..0000000000
--- a/docs/reference/cli/groups.md
+++ /dev/null
@@ -1,28 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: groups
-description: Manage groups
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage groups
-
-Aliases:
-
-* group
-
-## Usage
-
-```console
-coder groups
-```
-
-## Subcommands
-
-| Name                                      | Purpose             |
-|-------------------------------------------|---------------------|
-| [<code>create</code>](./groups_create.md) | Create a user group |
-| [<code>list</code>](./groups_list.md)     | List user groups    |
-| [<code>edit</code>](./groups_edit.md)     | Edit a user group   |
-| [<code>delete</code>](./groups_delete.md) | Delete a user group |
diff --git a/docs/reference/cli/groups_create.md b/docs/reference/cli/groups/create.md
similarity index 97%
rename from docs/reference/cli/groups_create.md
rename to docs/reference/cli/groups/create.md
index 368f7095e3..4753d8fa0c 100644
--- a/docs/reference/cli/groups_create.md
+++ b/docs/reference/cli/groups/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: groups create
+title: "`coder groups create`"
 description: Create a user group
 ---
 
diff --git a/docs/reference/cli/groups_delete.md b/docs/reference/cli/groups/delete.md
similarity index 94%
rename from docs/reference/cli/groups_delete.md
rename to docs/reference/cli/groups/delete.md
index a825db2807..b9667d006d 100644
--- a/docs/reference/cli/groups_delete.md
+++ b/docs/reference/cli/groups/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: groups delete
+title: "`coder groups delete`"
 description: Delete a user group
 ---
 
diff --git a/docs/reference/cli/groups_edit.md b/docs/reference/cli/groups/edit.md
similarity index 97%
rename from docs/reference/cli/groups_edit.md
rename to docs/reference/cli/groups/edit.md
index 2c345ee4bf..9e6e0a6f81 100644
--- a/docs/reference/cli/groups_edit.md
+++ b/docs/reference/cli/groups/edit.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: groups edit
+title: "`coder groups edit`"
 description: Edit a user group
 ---
 
diff --git a/docs/reference/cli/groups/index.md b/docs/reference/cli/groups/index.md
new file mode 100644
index 0000000000..11a02e2ac1
--- /dev/null
+++ b/docs/reference/cli/groups/index.md
@@ -0,0 +1,28 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder groups`"
+description: Manage groups
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage groups
+
+Aliases:
+
+* group
+
+## Usage
+
+```console
+coder groups
+```
+
+## Subcommands
+
+| Name                               | Purpose             |
+|------------------------------------|---------------------|
+| [<code>create</code>](./create.md) | Create a user group |
+| [<code>list</code>](./list.md)     | List user groups    |
+| [<code>edit</code>](./edit.md)     | Edit a user group   |
+| [<code>delete</code>](./delete.md) | Delete a user group |
diff --git a/docs/reference/cli/groups_list.md b/docs/reference/cli/groups/list.md
similarity index 97%
rename from docs/reference/cli/groups_list.md
rename to docs/reference/cli/groups/list.md
index 00bbef6b06..c80b293e74 100644
--- a/docs/reference/cli/groups_list.md
+++ b/docs/reference/cli/groups/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: groups list
+title: "`coder groups list`"
 description: List user groups
 ---
 
diff --git a/docs/reference/cli/index.md b/docs/reference/cli/index.md
index b4cb444f24..a03f14c909 100644
--- a/docs/reference/cli/index.md
+++ b/docs/reference/cli/index.md
@@ -28,57 +28,57 @@ Coder — A tool for provisioning self-hosted development environments with Terr
 
 ## Subcommands
 
-| Name                                                         | Purpose                                                                                                                      |
-|--------------------------------------------------------------|------------------------------------------------------------------------------------------------------------------------------|
-| [<code>completion</code>](./completion.md)                   | Install or update shell completion scripts for the detected or chosen shell.                                                 |
-| [<code>dotfiles</code>](./dotfiles.md)                       | Personalize your workspace by applying a canonical dotfiles repository                                                       |
-| [<code>external-auth</code>](./external-auth.md)             | Manage external authentication                                                                                               |
-| [<code>login</code>](./login.md)                             | Authenticate with Coder deployment                                                                                           |
-| [<code>logout</code>](./logout.md)                           | Unauthenticate your local session                                                                                            |
-| [<code>netcheck</code>](./netcheck.md)                       | Print network debug information for DERP and STUN                                                                            |
-| [<code>notifications</code>](./notifications.md)             | Manage Coder notifications                                                                                                   |
-| [<code>oauth2-provider</code>](./oauth2-provider.md)         | Manage Coder OAuth2 provider settings                                                                                        |
-| [<code>organizations</code>](./organizations.md)             | Organization related commands                                                                                                |
-| [<code>port-forward</code>](./port-forward.md)               | Forward ports from a workspace to the local machine. For reverse port forwarding, use "coder ssh -R".                        |
-| [<code>publickey</code>](./publickey.md)                     | Output your Coder public key used for Git operations                                                                         |
-| [<code>reset-password</code>](./reset-password.md)           | Directly connect to the database to reset a user's password                                                                  |
-| [<code>secret</code>](./secret.md)                           | Manage secrets                                                                                                               |
-| [<code>state</code>](./state.md)                             | Manually manage Terraform state to fix broken workspaces                                                                     |
-| [<code>templates</code>](./templates.md)                     | Manage templates                                                                                                             |
-| [<code>tokens</code>](./tokens.md)                           | Manage personal access tokens                                                                                                |
-| [<code>users</code>](./users.md)                             | Manage users                                                                                                                 |
-| [<code>version</code>](./version.md)                         | Show coder version                                                                                                           |
-| [<code>autoupdate</code>](./autoupdate.md)                   | Toggle auto-update policy for a workspace                                                                                    |
-| [<code>config-ssh</code>](./config-ssh.md)                   | Add an SSH Host entry for your workspaces "ssh workspace.coder"                                                              |
-| [<code>create</code>](./create.md)                           | Create a workspace                                                                                                           |
-| [<code>delete</code>](./delete.md)                           | Delete a workspace                                                                                                           |
-| [<code>favorite</code>](./favorite.md)                       | Add a workspace to your favorites                                                                                            |
-| [<code>list</code>](./list.md)                               | List workspaces                                                                                                              |
-| [<code>logs</code>](./logs.md)                               | View logs for a workspace                                                                                                    |
-| [<code>open</code>](./open.md)                               | Open a workspace                                                                                                             |
-| [<code>ping</code>](./ping.md)                               | Ping a workspace                                                                                                             |
-| [<code>rename</code>](./rename.md)                           | Rename a workspace                                                                                                           |
-| [<code>restart</code>](./restart.md)                         | Restart a workspace                                                                                                          |
-| [<code>schedule</code>](./schedule.md)                       | Schedule automated start and stop times for workspaces                                                                       |
-| [<code>show</code>](./show.md)                               | Display details of a workspace's resources and agents                                                                        |
-| [<code>speedtest</code>](./speedtest.md)                     | Run upload and download tests from your machine to a workspace                                                               |
-| [<code>ssh</code>](./ssh.md)                                 | Start a shell into a workspace or run a command                                                                              |
-| [<code>start</code>](./start.md)                             | Start a workspace                                                                                                            |
-| [<code>stat</code>](./stat.md)                               | Show resource usage for the current workspace.                                                                               |
-| [<code>stop</code>](./stop.md)                               | Stop a workspace                                                                                                             |
-| [<code>unfavorite</code>](./unfavorite.md)                   | Remove a workspace from your favorites                                                                                       |
-| [<code>update</code>](./update.md)                           | Will update and start a given workspace if it is out of date. If the workspace is already running, it will be stopped first. |
-| [<code>whoami</code>](./whoami.md)                           | Fetch authenticated user info for Coder deployment                                                                           |
-| [<code>support</code>](./support.md)                         | Commands for troubleshooting issues with a Coder deployment.                                                                 |
-| [<code>server</code>](./server.md)                           | Start a Coder server                                                                                                         |
-| [<code>provisioner</code>](./provisioner.md)                 | View and manage provisioner daemons and jobs                                                                                 |
-| [<code>ai-gateway</code>](./ai-gateway.md)                   | Manage AI Gateway                                                                                                            |
-| [<code>agent-firewall</code>](./agent-firewall.md)           | Network isolation tool for monitoring and restricting HTTP/HTTPS requests                                                    |
-| [<code>features</code>](./features.md)                       | List Enterprise features                                                                                                     |
-| [<code>licenses</code>](./licenses.md)                       | Add, delete, and list licenses                                                                                               |
-| [<code>groups</code>](./groups.md)                           | Manage groups                                                                                                                |
-| [<code>prebuilds</code>](./prebuilds.md)                     | Manage Coder prebuilds                                                                                                       |
-| [<code>external-workspaces</code>](./external-workspaces.md) | Create or manage external workspaces                                                                                         |
+| Name                                                               | Purpose                                                                                                                      |
+|--------------------------------------------------------------------|------------------------------------------------------------------------------------------------------------------------------|
+| [<code>completion</code>](./completion.md)                         | Install or update shell completion scripts for the detected or chosen shell.                                                 |
+| [<code>dotfiles</code>](./dotfiles.md)                             | Personalize your workspace by applying a canonical dotfiles repository                                                       |
+| [<code>external-auth</code>](./external-auth/index.md)             | Manage external authentication                                                                                               |
+| [<code>login</code>](./login/index.md)                             | Authenticate with Coder deployment                                                                                           |
+| [<code>logout</code>](./logout.md)                                 | Unauthenticate your local session                                                                                            |
+| [<code>netcheck</code>](./netcheck.md)                             | Print network debug information for DERP and STUN                                                                            |
+| [<code>notifications</code>](./notifications/index.md)             | Manage Coder notifications                                                                                                   |
+| [<code>oauth2-provider</code>](./oauth2-provider/index.md)         | Manage Coder OAuth2 provider settings                                                                                        |
+| [<code>organizations</code>](./organizations/index.md)             | Organization related commands                                                                                                |
+| [<code>port-forward</code>](./port-forward.md)                     | Forward ports from a workspace to the local machine. For reverse port forwarding, use "coder ssh -R".                        |
+| [<code>publickey</code>](./publickey.md)                           | Output your Coder public key used for Git operations                                                                         |
+| [<code>reset-password</code>](./reset-password.md)                 | Directly connect to the database to reset a user's password                                                                  |
+| [<code>secret</code>](./secret/index.md)                           | Manage secrets                                                                                                               |
+| [<code>state</code>](./state/index.md)                             | Manually manage Terraform state to fix broken workspaces                                                                     |
+| [<code>templates</code>](./templates/index.md)                     | Manage templates                                                                                                             |
+| [<code>tokens</code>](./tokens/index.md)                           | Manage personal access tokens                                                                                                |
+| [<code>users</code>](./users/index.md)                             | Manage users                                                                                                                 |
+| [<code>version</code>](./version.md)                               | Show coder version                                                                                                           |
+| [<code>autoupdate</code>](./autoupdate.md)                         | Toggle auto-update policy for a workspace                                                                                    |
+| [<code>config-ssh</code>](./config-ssh.md)                         | Add an SSH Host entry for your workspaces "ssh workspace.coder"                                                              |
+| [<code>create</code>](./create.md)                                 | Create a workspace                                                                                                           |
+| [<code>delete</code>](./delete.md)                                 | Delete a workspace                                                                                                           |
+| [<code>favorite</code>](./favorite.md)                             | Add a workspace to your favorites                                                                                            |
+| [<code>list</code>](./list.md)                                     | List workspaces                                                                                                              |
+| [<code>logs</code>](./logs.md)                                     | View logs for a workspace                                                                                                    |
+| [<code>open</code>](./open/index.md)                               | Open a workspace                                                                                                             |
+| [<code>ping</code>](./ping.md)                                     | Ping a workspace                                                                                                             |
+| [<code>rename</code>](./rename.md)                                 | Rename a workspace                                                                                                           |
+| [<code>restart</code>](./restart.md)                               | Restart a workspace                                                                                                          |
+| [<code>schedule</code>](./schedule/index.md)                       | Schedule automated start and stop times for workspaces                                                                       |
+| [<code>show</code>](./show.md)                                     | Display details of a workspace's resources and agents                                                                        |
+| [<code>speedtest</code>](./speedtest.md)                           | Run upload and download tests from your machine to a workspace                                                               |
+| [<code>ssh</code>](./ssh.md)                                       | Start a shell into a workspace or run a command                                                                              |
+| [<code>start</code>](./start.md)                                   | Start a workspace                                                                                                            |
+| [<code>stat</code>](./stat/index.md)                               | Show resource usage for the current workspace.                                                                               |
+| [<code>stop</code>](./stop.md)                                     | Stop a workspace                                                                                                             |
+| [<code>unfavorite</code>](./unfavorite.md)                         | Remove a workspace from your favorites                                                                                       |
+| [<code>update</code>](./update.md)                                 | Will update and start a given workspace if it is out of date. If the workspace is already running, it will be stopped first. |
+| [<code>whoami</code>](./whoami.md)                                 | Fetch authenticated user info for Coder deployment                                                                           |
+| [<code>support</code>](./support/index.md)                         | Commands for troubleshooting issues with a Coder deployment.                                                                 |
+| [<code>server</code>](./server/index.md)                           | Start a Coder server                                                                                                         |
+| [<code>provisioner</code>](./provisioner/index.md)                 | View and manage provisioner daemons and jobs                                                                                 |
+| [<code>ai-gateway</code>](./ai-gateway/index.md)                   | Manage AI Gateway                                                                                                            |
+| [<code>agent-firewall</code>](./agent-firewall.md)                 | Network isolation tool for monitoring and restricting HTTP/HTTPS requests                                                    |
+| [<code>features</code>](./features/index.md)                       | List Enterprise features                                                                                                     |
+| [<code>licenses</code>](./licenses/index.md)                       | Add, delete, and list licenses                                                                                               |
+| [<code>groups</code>](./groups/index.md)                           | Manage groups                                                                                                                |
+| [<code>prebuilds</code>](./prebuilds/index.md)                     | Manage Coder prebuilds                                                                                                       |
+| [<code>external-workspaces</code>](./external-workspaces/index.md) | Create or manage external workspaces                                                                                         |
 
 ## Options
 
diff --git a/docs/reference/cli/licenses.md b/docs/reference/cli/licenses.md
deleted file mode 100644
index 3dcb24dd4c..0000000000
--- a/docs/reference/cli/licenses.md
+++ /dev/null
@@ -1,27 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: licenses
-description: "Add, delete, and list licenses"
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Add, delete, and list licenses
-
-Aliases:
-
-* license
-
-## Usage
-
-```console
-coder licenses
-```
-
-## Subcommands
-
-| Name                                        | Purpose                           |
-|---------------------------------------------|-----------------------------------|
-| [<code>add</code>](./licenses_add.md)       | Add license to Coder deployment   |
-| [<code>list</code>](./licenses_list.md)     | List licenses (including expired) |
-| [<code>delete</code>](./licenses_delete.md) | Delete license by ID              |
diff --git a/docs/reference/cli/licenses_add.md b/docs/reference/cli/licenses/add.md
similarity index 95%
rename from docs/reference/cli/licenses_add.md
rename to docs/reference/cli/licenses/add.md
index 7d04b56e50..d4649e29c0 100644
--- a/docs/reference/cli/licenses_add.md
+++ b/docs/reference/cli/licenses/add.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: licenses add
+title: "`coder licenses add`"
 description: Add license to Coder deployment
 ---
 
diff --git a/docs/reference/cli/licenses_delete.md b/docs/reference/cli/licenses/delete.md
similarity index 87%
rename from docs/reference/cli/licenses_delete.md
rename to docs/reference/cli/licenses/delete.md
index 974a7d6da9..5ad1b01e14 100644
--- a/docs/reference/cli/licenses_delete.md
+++ b/docs/reference/cli/licenses/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: licenses delete
+title: "`coder licenses delete`"
 description: Delete license by ID
 ---
 
diff --git a/docs/reference/cli/licenses/index.md b/docs/reference/cli/licenses/index.md
new file mode 100644
index 0000000000..8a77910356
--- /dev/null
+++ b/docs/reference/cli/licenses/index.md
@@ -0,0 +1,27 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder licenses`"
+description: "Add, delete, and list licenses"
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Add, delete, and list licenses
+
+Aliases:
+
+* license
+
+## Usage
+
+```console
+coder licenses
+```
+
+## Subcommands
+
+| Name                               | Purpose                           |
+|------------------------------------|-----------------------------------|
+| [<code>add</code>](./add.md)       | Add license to Coder deployment   |
+| [<code>list</code>](./list.md)     | List licenses (including expired) |
+| [<code>delete</code>](./delete.md) | Delete license by ID              |
diff --git a/docs/reference/cli/licenses_list.md b/docs/reference/cli/licenses/list.md
similarity index 96%
rename from docs/reference/cli/licenses_list.md
rename to docs/reference/cli/licenses/list.md
index f5f4a03734..ef690b8abd 100644
--- a/docs/reference/cli/licenses_list.md
+++ b/docs/reference/cli/licenses/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: licenses list
+title: "`coder licenses list`"
 description: "List licenses (including expired)"
 ---
 
diff --git a/docs/reference/cli/list.md b/docs/reference/cli/list.md
index 8324fa8f72..e90339906f 100644
--- a/docs/reference/cli/list.md
+++ b/docs/reference/cli/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: list
+title: "`coder list`"
 description: List workspaces
 ---
 
diff --git a/docs/reference/cli/login.md b/docs/reference/cli/login/index.md
similarity index 95%
rename from docs/reference/cli/login.md
rename to docs/reference/cli/login/index.md
index 1143211191..3112baa220 100644
--- a/docs/reference/cli/login.md
+++ b/docs/reference/cli/login/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: login
+title: "`coder login`"
 description: Authenticate with Coder deployment
 ---
 
@@ -22,9 +22,9 @@ By default, the session token is stored in the operating system keyring on macOS
 
 ## Subcommands
 
-| Name                                   | Purpose                         |
-|----------------------------------------|---------------------------------|
-| [<code>token</code>](./login_token.md) | Print the current session token |
+| Name                             | Purpose                         |
+|----------------------------------|---------------------------------|
+| [<code>token</code>](./token.md) | Print the current session token |
 
 ## Options
 
diff --git a/docs/reference/cli/login_token.md b/docs/reference/cli/login/token.md
similarity index 91%
rename from docs/reference/cli/login_token.md
rename to docs/reference/cli/login/token.md
index 6354c83c4d..1f104b1a74 100644
--- a/docs/reference/cli/login_token.md
+++ b/docs/reference/cli/login/token.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: login token
+title: "`coder login token`"
 description: Print the current session token
 ---
 
diff --git a/docs/reference/cli/logout.md b/docs/reference/cli/logout.md
index 4bfefd16bb..478b1f0a2f 100644
--- a/docs/reference/cli/logout.md
+++ b/docs/reference/cli/logout.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: logout
+title: "`coder logout`"
 description: Unauthenticate your local session
 ---
 
diff --git a/docs/reference/cli/logs.md b/docs/reference/cli/logs.md
index 5b1814d79a..37001761f1 100644
--- a/docs/reference/cli/logs.md
+++ b/docs/reference/cli/logs.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: logs
+title: "`coder logs`"
 description: View logs for a workspace
 ---
 
diff --git a/docs/reference/cli/netcheck.md b/docs/reference/cli/netcheck.md
index 5df25cd52f..c86ed15a0e 100644
--- a/docs/reference/cli/netcheck.md
+++ b/docs/reference/cli/netcheck.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: netcheck
+title: "`coder netcheck`"
 description: Print network debug information for DERP and STUN
 ---
 
diff --git a/docs/reference/cli/notifications_custom.md b/docs/reference/cli/notifications/custom.md
similarity index 85%
rename from docs/reference/cli/notifications_custom.md
rename to docs/reference/cli/notifications/custom.md
index 470ab927e2..e8e1fc402f 100644
--- a/docs/reference/cli/notifications_custom.md
+++ b/docs/reference/cli/notifications/custom.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: notifications custom
+title: "`coder notifications custom`"
 description: Send a custom notification
 ---
 
diff --git a/docs/reference/cli/notifications.md b/docs/reference/cli/notifications/index.md
similarity index 65%
rename from docs/reference/cli/notifications.md
rename to docs/reference/cli/notifications/index.md
index 32ef81fe4d..e40b2cb781 100644
--- a/docs/reference/cli/notifications.md
+++ b/docs/reference/cli/notifications/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: notifications
+title: "`coder notifications`"
 description: Manage Coder notifications
 ---
 
@@ -45,9 +45,9 @@ targeting other users or groups is currently not supported:
 
 ## Subcommands
 
-| Name                                             | Purpose                    |
-|--------------------------------------------------|----------------------------|
-| [<code>pause</code>](./notifications_pause.md)   | Pause notifications        |
-| [<code>resume</code>](./notifications_resume.md) | Resume notifications       |
-| [<code>test</code>](./notifications_test.md)     | Send a test notification   |
-| [<code>custom</code>](./notifications_custom.md) | Send a custom notification |
+| Name                               | Purpose                    |
+|------------------------------------|----------------------------|
+| [<code>pause</code>](./pause.md)   | Pause notifications        |
+| [<code>resume</code>](./resume.md) | Resume notifications       |
+| [<code>test</code>](./test.md)     | Send a test notification   |
+| [<code>custom</code>](./custom.md) | Send a custom notification |
diff --git a/docs/reference/cli/notifications_pause.md b/docs/reference/cli/notifications/pause.md
similarity index 84%
rename from docs/reference/cli/notifications_pause.md
rename to docs/reference/cli/notifications/pause.md
index 92edf43880..b02504ea1a 100644
--- a/docs/reference/cli/notifications_pause.md
+++ b/docs/reference/cli/notifications/pause.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: notifications pause
+title: "`coder notifications pause`"
 description: Pause notifications
 ---
 
diff --git a/docs/reference/cli/notifications_resume.md b/docs/reference/cli/notifications/resume.md
similarity index 84%
rename from docs/reference/cli/notifications_resume.md
rename to docs/reference/cli/notifications/resume.md
index eedc58a094..6e4a32e7e1 100644
--- a/docs/reference/cli/notifications_resume.md
+++ b/docs/reference/cli/notifications/resume.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: notifications resume
+title: "`coder notifications resume`"
 description: Resume notifications
 ---
 
diff --git a/docs/reference/cli/notifications_test.md b/docs/reference/cli/notifications/test.md
similarity index 85%
rename from docs/reference/cli/notifications_test.md
rename to docs/reference/cli/notifications/test.md
index b6b91d10fe..83bd915731 100644
--- a/docs/reference/cli/notifications_test.md
+++ b/docs/reference/cli/notifications/test.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: notifications test
+title: "`coder notifications test`"
 description: Send a test notification
 ---
 
diff --git a/docs/reference/cli/oauth2-provider_dcr_disable.md b/docs/reference/cli/oauth2-provider/dcr/disable.md
similarity index 84%
rename from docs/reference/cli/oauth2-provider_dcr_disable.md
rename to docs/reference/cli/oauth2-provider/dcr/disable.md
index 893655664a..d8206083bf 100644
--- a/docs/reference/cli/oauth2-provider_dcr_disable.md
+++ b/docs/reference/cli/oauth2-provider/dcr/disable.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: oauth2-provider dcr disable
+title: "`coder oauth2-provider dcr disable`"
 description: Disable OAuth2 dynamic client registration
 ---
 
diff --git a/docs/reference/cli/oauth2-provider_dcr_enable.md b/docs/reference/cli/oauth2-provider/dcr/enable.md
similarity index 85%
rename from docs/reference/cli/oauth2-provider_dcr_enable.md
rename to docs/reference/cli/oauth2-provider/dcr/enable.md
index 123a8a5113..ab4e553095 100644
--- a/docs/reference/cli/oauth2-provider_dcr_enable.md
+++ b/docs/reference/cli/oauth2-provider/dcr/enable.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: oauth2-provider dcr enable
+title: "`coder oauth2-provider dcr enable`"
 description: Enable OAuth2 dynamic client registration
 ---
 
diff --git a/docs/reference/cli/oauth2-provider/dcr/index.md b/docs/reference/cli/oauth2-provider/dcr/index.md
new file mode 100644
index 0000000000..6cc27a6fe3
--- /dev/null
+++ b/docs/reference/cli/oauth2-provider/dcr/index.md
@@ -0,0 +1,22 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder oauth2-provider dcr`"
+description: "Manage OAuth2 dynamic client registration (RFC 7591)"
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage OAuth2 dynamic client registration (RFC 7591)
+
+## Usage
+
+```console
+coder oauth2-provider dcr
+```
+
+## Subcommands
+
+| Name                                 | Purpose                                    |
+|--------------------------------------|--------------------------------------------|
+| [<code>enable</code>](./enable.md)   | Enable OAuth2 dynamic client registration  |
+| [<code>disable</code>](./disable.md) | Disable OAuth2 dynamic client registration |
diff --git a/docs/reference/cli/oauth2-provider.md b/docs/reference/cli/oauth2-provider/index.md
similarity index 68%
rename from docs/reference/cli/oauth2-provider.md
rename to docs/reference/cli/oauth2-provider/index.md
index 566f2681d5..129e0cdc58 100644
--- a/docs/reference/cli/oauth2-provider.md
+++ b/docs/reference/cli/oauth2-provider/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: oauth2-provider
+title: "`coder oauth2-provider`"
 description: Manage Coder OAuth2 provider settings
 ---
 
@@ -31,6 +31,6 @@ unaffected; only new self-registration attempts are rejected:
 
 ## Subcommands
 
-| Name                                         | Purpose                                              |
-|----------------------------------------------|------------------------------------------------------|
-| [<code>dcr</code>](./oauth2-provider_dcr.md) | Manage OAuth2 dynamic client registration (RFC 7591) |
+| Name                               | Purpose                                              |
+|------------------------------------|------------------------------------------------------|
+| [<code>dcr</code>](./dcr/index.md) | Manage OAuth2 dynamic client registration (RFC 7591) |
diff --git a/docs/reference/cli/oauth2-provider_dcr.md b/docs/reference/cli/oauth2-provider_dcr.md
deleted file mode 100644
index 38643b6848..0000000000
--- a/docs/reference/cli/oauth2-provider_dcr.md
+++ /dev/null
@@ -1,22 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: oauth2-provider dcr
-description: "Manage OAuth2 dynamic client registration (RFC 7591)"
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage OAuth2 dynamic client registration (RFC 7591)
-
-## Usage
-
-```console
-coder oauth2-provider dcr
-```
-
-## Subcommands
-
-| Name                                                     | Purpose                                    |
-|----------------------------------------------------------|--------------------------------------------|
-| [<code>enable</code>](./oauth2-provider_dcr_enable.md)   | Enable OAuth2 dynamic client registration  |
-| [<code>disable</code>](./oauth2-provider_dcr_disable.md) | Disable OAuth2 dynamic client registration |
diff --git a/docs/reference/cli/open.md b/docs/reference/cli/open.md
deleted file mode 100644
index 9d756d856f..0000000000
--- a/docs/reference/cli/open.md
+++ /dev/null
@@ -1,22 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: open
-description: Open a workspace
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Open a workspace
-
-## Usage
-
-```console
-coder open
-```
-
-## Subcommands
-
-| Name                                    | Purpose                             |
-|-----------------------------------------|-------------------------------------|
-| [<code>vscode</code>](./open_vscode.md) | Open a workspace in VS Code Desktop |
-| [<code>app</code>](./open_app.md)       | Open a workspace application.       |
diff --git a/docs/reference/cli/open_app.md b/docs/reference/cli/open/app.md
similarity index 96%
rename from docs/reference/cli/open_app.md
rename to docs/reference/cli/open/app.md
index 3301b0d380..e41ab034c5 100644
--- a/docs/reference/cli/open_app.md
+++ b/docs/reference/cli/open/app.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: open app
+title: "`coder open app`"
 description: Open a workspace application.
 ---
 
diff --git a/docs/reference/cli/open/index.md b/docs/reference/cli/open/index.md
new file mode 100644
index 0000000000..a1f3ec3bc3
--- /dev/null
+++ b/docs/reference/cli/open/index.md
@@ -0,0 +1,22 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder open`"
+description: Open a workspace
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Open a workspace
+
+## Usage
+
+```console
+coder open
+```
+
+## Subcommands
+
+| Name                               | Purpose                             |
+|------------------------------------|-------------------------------------|
+| [<code>vscode</code>](./vscode.md) | Open a workspace in VS Code Desktop |
+| [<code>app</code>](./app.md)       | Open a workspace application.       |
diff --git a/docs/reference/cli/open_vscode.md b/docs/reference/cli/open/vscode.md
similarity index 96%
rename from docs/reference/cli/open_vscode.md
rename to docs/reference/cli/open/vscode.md
index 207c94cf48..13251cf0ba 100644
--- a/docs/reference/cli/open_vscode.md
+++ b/docs/reference/cli/open/vscode.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: open vscode
+title: "`coder open vscode`"
 description: Open a workspace in VS Code Desktop
 ---
 
diff --git a/docs/reference/cli/organizations.md b/docs/reference/cli/organizations.md
deleted file mode 100644
index f7020cb5a6..0000000000
--- a/docs/reference/cli/organizations.md
+++ /dev/null
@@ -1,45 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: organizations
-description: Organization related commands
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Organization related commands
-
-Aliases:
-
-* organization
-* org
-* orgs
-
-## Usage
-
-```console
-coder organizations [flags] [subcommand]
-```
-
-## Subcommands
-
-| Name                                                 | Purpose                                                                                                                                                        |
-|------------------------------------------------------|----------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| [<code>show</code>](./organizations_show.md)         | Show the organization. Using "selected" will show the selected organization from the "--org" flag. Using "me" will show all organizations you are a member of. |
-| [<code>list</code>](./organizations_list.md)         | List all organizations                                                                                                                                         |
-| [<code>create</code>](./organizations_create.md)     | Create a new organization.                                                                                                                                     |
-| [<code>edit</code>](./organizations_edit.md)         | Edit organization settings.                                                                                                                                    |
-| [<code>delete</code>](./organizations_delete.md)     | Delete an organization                                                                                                                                         |
-| [<code>members</code>](./organizations_members.md)   | Manage organization members                                                                                                                                    |
-| [<code>roles</code>](./organizations_roles.md)       | Manage organization roles.                                                                                                                                     |
-| [<code>settings</code>](./organizations_settings.md) | Manage organization settings.                                                                                                                                  |
-
-## Options
-
-### -O, --org
-
-|             |                                  |
-|-------------|----------------------------------|
-| Type        | <code>string</code>              |
-| Environment | <code>$CODER_ORGANIZATION</code> |
-
-Select which organization (uuid or name) to use.
diff --git a/docs/reference/cli/organizations_create.md b/docs/reference/cli/organizations/create.md
similarity index 91%
rename from docs/reference/cli/organizations_create.md
rename to docs/reference/cli/organizations/create.md
index 72f0d0f1b3..dd2a39c42f 100644
--- a/docs/reference/cli/organizations_create.md
+++ b/docs/reference/cli/organizations/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations create
+title: "`coder organizations create`"
 description: Create a new organization.
 ---
 
diff --git a/docs/reference/cli/organizations_delete.md b/docs/reference/cli/organizations/delete.md
similarity index 91%
rename from docs/reference/cli/organizations_delete.md
rename to docs/reference/cli/organizations/delete.md
index ccd47507d5..73f309e75a 100644
--- a/docs/reference/cli/organizations_delete.md
+++ b/docs/reference/cli/organizations/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations delete
+title: "`coder organizations delete`"
 description: Delete an organization
 ---
 
diff --git a/docs/reference/cli/organizations_edit.md b/docs/reference/cli/organizations/edit.md
similarity index 97%
rename from docs/reference/cli/organizations_edit.md
rename to docs/reference/cli/organizations/edit.md
index 78e3a0516a..3d6d6ee795 100644
--- a/docs/reference/cli/organizations_edit.md
+++ b/docs/reference/cli/organizations/edit.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations edit
+title: "`coder organizations edit`"
 description: Edit organization settings.
 ---
 
diff --git a/docs/reference/cli/organizations/index.md b/docs/reference/cli/organizations/index.md
new file mode 100644
index 0000000000..a3b9b8ea64
--- /dev/null
+++ b/docs/reference/cli/organizations/index.md
@@ -0,0 +1,45 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder organizations`"
+description: Organization related commands
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Organization related commands
+
+Aliases:
+
+* organization
+* org
+* orgs
+
+## Usage
+
+```console
+coder organizations [flags] [subcommand]
+```
+
+## Subcommands
+
+| Name                                         | Purpose                                                                                                                                                        |
+|----------------------------------------------|----------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| [<code>show</code>](./show.md)               | Show the organization. Using "selected" will show the selected organization from the "--org" flag. Using "me" will show all organizations you are a member of. |
+| [<code>list</code>](./list.md)               | List all organizations                                                                                                                                         |
+| [<code>create</code>](./create.md)           | Create a new organization.                                                                                                                                     |
+| [<code>edit</code>](./edit.md)               | Edit organization settings.                                                                                                                                    |
+| [<code>delete</code>](./delete.md)           | Delete an organization                                                                                                                                         |
+| [<code>members</code>](./members/index.md)   | Manage organization members                                                                                                                                    |
+| [<code>roles</code>](./roles/index.md)       | Manage organization roles.                                                                                                                                     |
+| [<code>settings</code>](./settings/index.md) | Manage organization settings.                                                                                                                                  |
+
+## Options
+
+### -O, --org
+
+|             |                                  |
+|-------------|----------------------------------|
+| Type        | <code>string</code>              |
+| Environment | <code>$CODER_ORGANIZATION</code> |
+
+Select which organization (uuid or name) to use.
diff --git a/docs/reference/cli/organizations_list.md b/docs/reference/cli/organizations/list.md
similarity index 96%
rename from docs/reference/cli/organizations_list.md
rename to docs/reference/cli/organizations/list.md
index 2bec17415c..ff41412df6 100644
--- a/docs/reference/cli/organizations_list.md
+++ b/docs/reference/cli/organizations/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations list
+title: "`coder organizations list`"
 description: List all organizations
 ---
 
diff --git a/docs/reference/cli/organizations_members_add.md b/docs/reference/cli/organizations/members/add.md
similarity index 86%
rename from docs/reference/cli/organizations_members_add.md
rename to docs/reference/cli/organizations/members/add.md
index 3bd1216662..e9e071c0e7 100644
--- a/docs/reference/cli/organizations_members_add.md
+++ b/docs/reference/cli/organizations/members/add.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations members add
+title: "`coder organizations members add`"
 description: Add a new member to the current organization
 ---
 
diff --git a/docs/reference/cli/organizations_members_edit-roles.md b/docs/reference/cli/organizations/members/edit-roles.md
similarity index 85%
rename from docs/reference/cli/organizations_members_edit-roles.md
rename to docs/reference/cli/organizations/members/edit-roles.md
index eabf57d6bb..4d09c8c5cd 100644
--- a/docs/reference/cli/organizations_members_edit-roles.md
+++ b/docs/reference/cli/organizations/members/edit-roles.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations members edit-roles
+title: "`coder organizations members edit-roles`"
 description: "Edit organization member's roles"
 ---
 
diff --git a/docs/reference/cli/organizations/members/index.md b/docs/reference/cli/organizations/members/index.md
new file mode 100644
index 0000000000..a5792f86da
--- /dev/null
+++ b/docs/reference/cli/organizations/members/index.md
@@ -0,0 +1,28 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder organizations members`"
+description: Manage organization members
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage organization members
+
+Aliases:
+
+* member
+
+## Usage
+
+```console
+coder organizations members
+```
+
+## Subcommands
+
+| Name                                       | Purpose                                         |
+|--------------------------------------------|-------------------------------------------------|
+| [<code>list</code>](./list.md)             | List all organization members                   |
+| [<code>edit-roles</code>](./edit-roles.md) | Edit organization member's roles                |
+| [<code>add</code>](./add.md)               | Add a new member to the current organization    |
+| [<code>remove</code>](./remove.md)         | Remove a new member to the current organization |
diff --git a/docs/reference/cli/organizations_members_list.md b/docs/reference/cli/organizations/members/list.md
similarity index 96%
rename from docs/reference/cli/organizations_members_list.md
rename to docs/reference/cli/organizations/members/list.md
index dc339704db..52a3c8ce25 100644
--- a/docs/reference/cli/organizations_members_list.md
+++ b/docs/reference/cli/organizations/members/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations members list
+title: "`coder organizations members list`"
 description: List all organization members
 ---
 
diff --git a/docs/reference/cli/organizations_members_remove.md b/docs/reference/cli/organizations/members/remove.md
similarity index 86%
rename from docs/reference/cli/organizations_members_remove.md
rename to docs/reference/cli/organizations/members/remove.md
index 39b58e052b..0c42a22fa3 100644
--- a/docs/reference/cli/organizations_members_remove.md
+++ b/docs/reference/cli/organizations/members/remove.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations members remove
+title: "`coder organizations members remove`"
 description: Remove a new member to the current organization
 ---
 
diff --git a/docs/reference/cli/organizations_roles_create.md b/docs/reference/cli/organizations/roles/create.md
similarity index 95%
rename from docs/reference/cli/organizations_roles_create.md
rename to docs/reference/cli/organizations/roles/create.md
index 36dc5eca8e..5040f6eba9 100644
--- a/docs/reference/cli/organizations_roles_create.md
+++ b/docs/reference/cli/organizations/roles/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations roles create
+title: "`coder organizations roles create`"
 description: Create a new organization custom role
 ---
 
diff --git a/docs/reference/cli/organizations/roles/index.md b/docs/reference/cli/organizations/roles/index.md
new file mode 100644
index 0000000000..46710d9137
--- /dev/null
+++ b/docs/reference/cli/organizations/roles/index.md
@@ -0,0 +1,27 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder organizations roles`"
+description: Manage organization roles.
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage organization roles.
+
+Aliases:
+
+* role
+
+## Usage
+
+```console
+coder organizations roles
+```
+
+## Subcommands
+
+| Name                               | Purpose                               |
+|------------------------------------|---------------------------------------|
+| [<code>show</code>](./show.md)     | Show role(s)                          |
+| [<code>update</code>](./update.md) | Update an organization custom role    |
+| [<code>create</code>](./create.md) | Create a new organization custom role |
diff --git a/docs/reference/cli/organizations_roles_show.md b/docs/reference/cli/organizations/roles/show.md
similarity index 95%
rename from docs/reference/cli/organizations_roles_show.md
rename to docs/reference/cli/organizations/roles/show.md
index 8bf9969599..8d9ce05dfc 100644
--- a/docs/reference/cli/organizations_roles_show.md
+++ b/docs/reference/cli/organizations/roles/show.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations roles show
+title: "`coder organizations roles show`"
 description: "Show role(s)"
 ---
 
diff --git a/docs/reference/cli/organizations_roles_update.md b/docs/reference/cli/organizations/roles/update.md
similarity index 97%
rename from docs/reference/cli/organizations_roles_update.md
rename to docs/reference/cli/organizations/roles/update.md
index d323e622b5..1ea80e4e37 100644
--- a/docs/reference/cli/organizations_roles_update.md
+++ b/docs/reference/cli/organizations/roles/update.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations roles update
+title: "`coder organizations roles update`"
 description: Update an organization custom role
 ---
 
diff --git a/docs/reference/cli/organizations/settings/index.md b/docs/reference/cli/organizations/settings/index.md
new file mode 100644
index 0000000000..0542e85c54
--- /dev/null
+++ b/docs/reference/cli/organizations/settings/index.md
@@ -0,0 +1,26 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder organizations settings`"
+description: Manage organization settings.
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage organization settings.
+
+Aliases:
+
+* setting
+
+## Usage
+
+```console
+coder organizations settings
+```
+
+## Subcommands
+
+| Name                                 | Purpose                                 |
+|--------------------------------------|-----------------------------------------|
+| [<code>show</code>](./show/index.md) | Outputs specified organization setting. |
+| [<code>set</code>](./set/index.md)   | Update specified organization setting.  |
diff --git a/docs/reference/cli/organizations_settings_set_group-sync.md b/docs/reference/cli/organizations/settings/set/group-sync.md
similarity index 84%
rename from docs/reference/cli/organizations_settings_set_group-sync.md
rename to docs/reference/cli/organizations/settings/set/group-sync.md
index 6a393933cb..8d6ce46887 100644
--- a/docs/reference/cli/organizations_settings_set_group-sync.md
+++ b/docs/reference/cli/organizations/settings/set/group-sync.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings set group-sync
+title: "`coder organizations settings set group-sync`"
 description: Group sync settings to sync groups from an IdP.
 ---
 
diff --git a/docs/reference/cli/organizations/settings/set/index.md b/docs/reference/cli/organizations/settings/set/index.md
new file mode 100644
index 0000000000..d8dfff234c
--- /dev/null
+++ b/docs/reference/cli/organizations/settings/set/index.md
@@ -0,0 +1,32 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder organizations settings set`"
+description: Update specified organization setting.
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Update specified organization setting.
+
+## Usage
+
+```console
+coder organizations settings set
+```
+
+## Description
+
+```console
+  - Update group sync settings.:
+
+     $ coder organization settings set groupsync < input.json
+```
+
+## Subcommands
+
+| Name                                                     | Purpose                                                                  |
+|----------------------------------------------------------|--------------------------------------------------------------------------|
+| [<code>group-sync</code>](./group-sync.md)               | Group sync settings to sync groups from an IdP.                          |
+| [<code>role-sync</code>](./role-sync.md)                 | Role sync settings to sync organization roles from an IdP.               |
+| [<code>organization-sync</code>](./organization-sync.md) | Organization sync settings to sync organization memberships from an IdP. |
+| [<code>workspace-sharing</code>](./workspace-sharing.md) | Workspace sharing settings for the organization.                         |
diff --git a/docs/reference/cli/organizations_settings_set_organization-sync.md b/docs/reference/cli/organizations/settings/set/organization-sync.md
similarity index 86%
rename from docs/reference/cli/organizations_settings_set_organization-sync.md
rename to docs/reference/cli/organizations/settings/set/organization-sync.md
index 4443bf9974..5db9d69b48 100644
--- a/docs/reference/cli/organizations_settings_set_organization-sync.md
+++ b/docs/reference/cli/organizations/settings/set/organization-sync.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings set organization-sync
+title: "`coder organizations settings set organization-sync`"
 description: Organization sync settings to sync organization memberships from an IdP.
 ---
 
diff --git a/docs/reference/cli/organizations_settings_set_role-sync.md b/docs/reference/cli/organizations/settings/set/role-sync.md
similarity index 85%
rename from docs/reference/cli/organizations_settings_set_role-sync.md
rename to docs/reference/cli/organizations/settings/set/role-sync.md
index 92a359c3be..cf71243640 100644
--- a/docs/reference/cli/organizations_settings_set_role-sync.md
+++ b/docs/reference/cli/organizations/settings/set/role-sync.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings set role-sync
+title: "`coder organizations settings set role-sync`"
 description: Role sync settings to sync organization roles from an IdP.
 ---
 
diff --git a/docs/reference/cli/organizations_settings_set_workspace-sharing.md b/docs/reference/cli/organizations/settings/set/workspace-sharing.md
similarity index 83%
rename from docs/reference/cli/organizations_settings_set_workspace-sharing.md
rename to docs/reference/cli/organizations/settings/set/workspace-sharing.md
index 58ff2d0c77..aa24413305 100644
--- a/docs/reference/cli/organizations_settings_set_workspace-sharing.md
+++ b/docs/reference/cli/organizations/settings/set/workspace-sharing.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings set workspace-sharing
+title: "`coder organizations settings set workspace-sharing`"
 description: Workspace sharing settings for the organization.
 ---
 
diff --git a/docs/reference/cli/organizations_settings_show_group-sync.md b/docs/reference/cli/organizations/settings/show/group-sync.md
similarity index 84%
rename from docs/reference/cli/organizations_settings_show_group-sync.md
rename to docs/reference/cli/organizations/settings/show/group-sync.md
index 080e02518e..76e2d39f5a 100644
--- a/docs/reference/cli/organizations_settings_show_group-sync.md
+++ b/docs/reference/cli/organizations/settings/show/group-sync.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings show group-sync
+title: "`coder organizations settings show group-sync`"
 description: Group sync settings to sync groups from an IdP.
 ---
 
diff --git a/docs/reference/cli/organizations/settings/show/index.md b/docs/reference/cli/organizations/settings/show/index.md
new file mode 100644
index 0000000000..1f7ecc72af
--- /dev/null
+++ b/docs/reference/cli/organizations/settings/show/index.md
@@ -0,0 +1,32 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder organizations settings show`"
+description: Outputs specified organization setting.
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Outputs specified organization setting.
+
+## Usage
+
+```console
+coder organizations settings show
+```
+
+## Description
+
+```console
+  - Output group sync settings.:
+
+     $ coder organization settings show groupsync
+```
+
+## Subcommands
+
+| Name                                                     | Purpose                                                                  |
+|----------------------------------------------------------|--------------------------------------------------------------------------|
+| [<code>group-sync</code>](./group-sync.md)               | Group sync settings to sync groups from an IdP.                          |
+| [<code>role-sync</code>](./role-sync.md)                 | Role sync settings to sync organization roles from an IdP.               |
+| [<code>organization-sync</code>](./organization-sync.md) | Organization sync settings to sync organization memberships from an IdP. |
+| [<code>workspace-sharing</code>](./workspace-sharing.md) | Workspace sharing settings for the organization.                         |
diff --git a/docs/reference/cli/organizations_settings_show_organization-sync.md b/docs/reference/cli/organizations/settings/show/organization-sync.md
similarity index 85%
rename from docs/reference/cli/organizations_settings_show_organization-sync.md
rename to docs/reference/cli/organizations/settings/show/organization-sync.md
index d677056ad3..60e1e24a80 100644
--- a/docs/reference/cli/organizations_settings_show_organization-sync.md
+++ b/docs/reference/cli/organizations/settings/show/organization-sync.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings show organization-sync
+title: "`coder organizations settings show organization-sync`"
 description: Organization sync settings to sync organization memberships from an IdP.
 ---
 
diff --git a/docs/reference/cli/organizations_settings_show_role-sync.md b/docs/reference/cli/organizations/settings/show/role-sync.md
similarity index 85%
rename from docs/reference/cli/organizations_settings_show_role-sync.md
rename to docs/reference/cli/organizations/settings/show/role-sync.md
index 2f38a7a2a3..79ca43a7b8 100644
--- a/docs/reference/cli/organizations_settings_show_role-sync.md
+++ b/docs/reference/cli/organizations/settings/show/role-sync.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings show role-sync
+title: "`coder organizations settings show role-sync`"
 description: Role sync settings to sync organization roles from an IdP.
 ---
 
diff --git a/docs/reference/cli/organizations_settings_show_workspace-sharing.md b/docs/reference/cli/organizations/settings/show/workspace-sharing.md
similarity index 83%
rename from docs/reference/cli/organizations_settings_show_workspace-sharing.md
rename to docs/reference/cli/organizations/settings/show/workspace-sharing.md
index 727a181e02..41b6bb24cc 100644
--- a/docs/reference/cli/organizations_settings_show_workspace-sharing.md
+++ b/docs/reference/cli/organizations/settings/show/workspace-sharing.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations settings show workspace-sharing
+title: "`coder organizations settings show workspace-sharing`"
 description: Workspace sharing settings for the organization.
 ---
 
diff --git a/docs/reference/cli/organizations_show.md b/docs/reference/cli/organizations/show.md
similarity index 98%
rename from docs/reference/cli/organizations_show.md
rename to docs/reference/cli/organizations/show.md
index 0c6c46d921..5cfe7fecbc 100644
--- a/docs/reference/cli/organizations_show.md
+++ b/docs/reference/cli/organizations/show.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: organizations show
+title: "`coder organizations show`"
 description: "Show the organization. Using \"selected\" will show the selected organization from the \"--org\" flag. Using \"me\" will show all organizations you are a member of."
 ---
 
diff --git a/docs/reference/cli/organizations_members.md b/docs/reference/cli/organizations_members.md
deleted file mode 100644
index 7cb0c8db47..0000000000
--- a/docs/reference/cli/organizations_members.md
+++ /dev/null
@@ -1,28 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: organizations members
-description: Manage organization members
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage organization members
-
-Aliases:
-
-* member
-
-## Usage
-
-```console
-coder organizations members
-```
-
-## Subcommands
-
-| Name                                                             | Purpose                                         |
-|------------------------------------------------------------------|-------------------------------------------------|
-| [<code>list</code>](./organizations_members_list.md)             | List all organization members                   |
-| [<code>edit-roles</code>](./organizations_members_edit-roles.md) | Edit organization member's roles                |
-| [<code>add</code>](./organizations_members_add.md)               | Add a new member to the current organization    |
-| [<code>remove</code>](./organizations_members_remove.md)         | Remove a new member to the current organization |
diff --git a/docs/reference/cli/organizations_roles.md b/docs/reference/cli/organizations_roles.md
deleted file mode 100644
index ec42653b8f..0000000000
--- a/docs/reference/cli/organizations_roles.md
+++ /dev/null
@@ -1,27 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: organizations roles
-description: Manage organization roles.
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage organization roles.
-
-Aliases:
-
-* role
-
-## Usage
-
-```console
-coder organizations roles
-```
-
-## Subcommands
-
-| Name                                                   | Purpose                               |
-|--------------------------------------------------------|---------------------------------------|
-| [<code>show</code>](./organizations_roles_show.md)     | Show role(s)                          |
-| [<code>update</code>](./organizations_roles_update.md) | Update an organization custom role    |
-| [<code>create</code>](./organizations_roles_create.md) | Create a new organization custom role |
diff --git a/docs/reference/cli/organizations_settings.md b/docs/reference/cli/organizations_settings.md
deleted file mode 100644
index 8b278a4cd9..0000000000
--- a/docs/reference/cli/organizations_settings.md
+++ /dev/null
@@ -1,26 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: organizations settings
-description: Manage organization settings.
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage organization settings.
-
-Aliases:
-
-* setting
-
-## Usage
-
-```console
-coder organizations settings
-```
-
-## Subcommands
-
-| Name                                                  | Purpose                                 |
-|-------------------------------------------------------|-----------------------------------------|
-| [<code>show</code>](./organizations_settings_show.md) | Outputs specified organization setting. |
-| [<code>set</code>](./organizations_settings_set.md)   | Update specified organization setting.  |
diff --git a/docs/reference/cli/organizations_settings_set.md b/docs/reference/cli/organizations_settings_set.md
deleted file mode 100644
index ccf32ca0df..0000000000
--- a/docs/reference/cli/organizations_settings_set.md
+++ /dev/null
@@ -1,32 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: organizations settings set
-description: Update specified organization setting.
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Update specified organization setting.
-
-## Usage
-
-```console
-coder organizations settings set
-```
-
-## Description
-
-```console
-  - Update group sync settings.:
-
-     $ coder organization settings set groupsync < input.json
-```
-
-## Subcommands
-
-| Name                                                                                | Purpose                                                                  |
-|-------------------------------------------------------------------------------------|--------------------------------------------------------------------------|
-| [<code>group-sync</code>](./organizations_settings_set_group-sync.md)               | Group sync settings to sync groups from an IdP.                          |
-| [<code>role-sync</code>](./organizations_settings_set_role-sync.md)                 | Role sync settings to sync organization roles from an IdP.               |
-| [<code>organization-sync</code>](./organizations_settings_set_organization-sync.md) | Organization sync settings to sync organization memberships from an IdP. |
-| [<code>workspace-sharing</code>](./organizations_settings_set_workspace-sharing.md) | Workspace sharing settings for the organization.                         |
diff --git a/docs/reference/cli/organizations_settings_show.md b/docs/reference/cli/organizations_settings_show.md
deleted file mode 100644
index 2dc033f5dc..0000000000
--- a/docs/reference/cli/organizations_settings_show.md
+++ /dev/null
@@ -1,32 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: organizations settings show
-description: Outputs specified organization setting.
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Outputs specified organization setting.
-
-## Usage
-
-```console
-coder organizations settings show
-```
-
-## Description
-
-```console
-  - Output group sync settings.:
-
-     $ coder organization settings show groupsync
-```
-
-## Subcommands
-
-| Name                                                                                 | Purpose                                                                  |
-|--------------------------------------------------------------------------------------|--------------------------------------------------------------------------|
-| [<code>group-sync</code>](./organizations_settings_show_group-sync.md)               | Group sync settings to sync groups from an IdP.                          |
-| [<code>role-sync</code>](./organizations_settings_show_role-sync.md)                 | Role sync settings to sync organization roles from an IdP.               |
-| [<code>organization-sync</code>](./organizations_settings_show_organization-sync.md) | Organization sync settings to sync organization memberships from an IdP. |
-| [<code>workspace-sharing</code>](./organizations_settings_show_workspace-sharing.md) | Workspace sharing settings for the organization.                         |
diff --git a/docs/reference/cli/ping.md b/docs/reference/cli/ping.md
index b7efca5e06..ec4dd429ec 100644
--- a/docs/reference/cli/ping.md
+++ b/docs/reference/cli/ping.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: ping
+title: "`coder ping`"
 description: Ping a workspace
 ---
 
diff --git a/docs/reference/cli/port-forward.md b/docs/reference/cli/port-forward.md
index 4319d1110b..d837ae9675 100644
--- a/docs/reference/cli/port-forward.md
+++ b/docs/reference/cli/port-forward.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: port-forward
+title: "`coder port-forward`"
 description: "Forward ports from a workspace to the local machine. For reverse port forwarding, use \"coder ssh -R\"."
 ---
 
diff --git a/docs/reference/cli/prebuilds.md b/docs/reference/cli/prebuilds/index.md
similarity index 64%
rename from docs/reference/cli/prebuilds.md
rename to docs/reference/cli/prebuilds/index.md
index 4aa5763a7b..44048753df 100644
--- a/docs/reference/cli/prebuilds.md
+++ b/docs/reference/cli/prebuilds/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: prebuilds
+title: "`coder prebuilds`"
 description: Manage Coder prebuilds
 ---
 
@@ -33,7 +33,7 @@ Administrators can use these commands to manage prebuilt workspace settings.
 
 ## Subcommands
 
-| Name                                         | Purpose          |
-|----------------------------------------------|------------------|
-| [<code>pause</code>](./prebuilds_pause.md)   | Pause prebuilds  |
-| [<code>resume</code>](./prebuilds_resume.md) | Resume prebuilds |
+| Name                               | Purpose          |
+|------------------------------------|------------------|
+| [<code>pause</code>](./pause.md)   | Pause prebuilds  |
+| [<code>resume</code>](./resume.md) | Resume prebuilds |
diff --git a/docs/reference/cli/prebuilds_pause.md b/docs/reference/cli/prebuilds/pause.md
similarity index 85%
rename from docs/reference/cli/prebuilds_pause.md
rename to docs/reference/cli/prebuilds/pause.md
index 96f3c95743..2acedb338a 100644
--- a/docs/reference/cli/prebuilds_pause.md
+++ b/docs/reference/cli/prebuilds/pause.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: prebuilds pause
+title: "`coder prebuilds pause`"
 description: Pause prebuilds
 ---
 
diff --git a/docs/reference/cli/prebuilds_resume.md b/docs/reference/cli/prebuilds/resume.md
similarity index 84%
rename from docs/reference/cli/prebuilds_resume.md
rename to docs/reference/cli/prebuilds/resume.md
index c258bd919a..319352f791 100644
--- a/docs/reference/cli/prebuilds_resume.md
+++ b/docs/reference/cli/prebuilds/resume.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: prebuilds resume
+title: "`coder prebuilds resume`"
 description: Resume prebuilds
 ---
 
diff --git a/docs/reference/cli/provisioner.md b/docs/reference/cli/provisioner.md
deleted file mode 100644
index 0c7fcd9c6e..0000000000
--- a/docs/reference/cli/provisioner.md
+++ /dev/null
@@ -1,28 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: provisioner
-description: View and manage provisioner daemons and jobs
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-View and manage provisioner daemons and jobs
-
-Aliases:
-
-* provisioners
-
-## Usage
-
-```console
-coder provisioner
-```
-
-## Subcommands
-
-| Name                                         | Purpose                                     |
-|----------------------------------------------|---------------------------------------------|
-| [<code>list</code>](./provisioner_list.md)   | List provisioner daemons in an organization |
-| [<code>jobs</code>](./provisioner_jobs.md)   | View and manage provisioner jobs            |
-| [<code>start</code>](./provisioner_start.md) | Run a provisioner daemon                    |
-| [<code>keys</code>](./provisioner_keys.md)   | Manage provisioner keys                     |
diff --git a/docs/reference/cli/provisioner/index.md b/docs/reference/cli/provisioner/index.md
new file mode 100644
index 0000000000..e20226bf90
--- /dev/null
+++ b/docs/reference/cli/provisioner/index.md
@@ -0,0 +1,28 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder provisioner`"
+description: View and manage provisioner daemons and jobs
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+View and manage provisioner daemons and jobs
+
+Aliases:
+
+* provisioners
+
+## Usage
+
+```console
+coder provisioner
+```
+
+## Subcommands
+
+| Name                                 | Purpose                                     |
+|--------------------------------------|---------------------------------------------|
+| [<code>list</code>](./list.md)       | List provisioner daemons in an organization |
+| [<code>jobs</code>](./jobs/index.md) | View and manage provisioner jobs            |
+| [<code>start</code>](./start.md)     | Run a provisioner daemon                    |
+| [<code>keys</code>](./keys/index.md) | Manage provisioner keys                     |
diff --git a/docs/reference/cli/provisioner_jobs_cancel.md b/docs/reference/cli/provisioner/jobs/cancel.md
similarity index 92%
rename from docs/reference/cli/provisioner_jobs_cancel.md
rename to docs/reference/cli/provisioner/jobs/cancel.md
index 5ae522036f..08596b7cef 100644
--- a/docs/reference/cli/provisioner_jobs_cancel.md
+++ b/docs/reference/cli/provisioner/jobs/cancel.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner jobs cancel
+title: "`coder provisioner jobs cancel`"
 description: Cancel a provisioner job
 ---
 
diff --git a/docs/reference/cli/provisioner/jobs/index.md b/docs/reference/cli/provisioner/jobs/index.md
new file mode 100644
index 0000000000..a004eb4849
--- /dev/null
+++ b/docs/reference/cli/provisioner/jobs/index.md
@@ -0,0 +1,26 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder provisioner jobs`"
+description: View and manage provisioner jobs
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+View and manage provisioner jobs
+
+Aliases:
+
+* job
+
+## Usage
+
+```console
+coder provisioner jobs
+```
+
+## Subcommands
+
+| Name                               | Purpose                  |
+|------------------------------------|--------------------------|
+| [<code>cancel</code>](./cancel.md) | Cancel a provisioner job |
+| [<code>list</code>](./list.md)     | List provisioner jobs    |
diff --git a/docs/reference/cli/provisioner_jobs_list.md b/docs/reference/cli/provisioner/jobs/list.md
similarity index 98%
rename from docs/reference/cli/provisioner_jobs_list.md
rename to docs/reference/cli/provisioner/jobs/list.md
index 93bb2c1c11..b78f445a9b 100644
--- a/docs/reference/cli/provisioner_jobs_list.md
+++ b/docs/reference/cli/provisioner/jobs/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner jobs list
+title: "`coder provisioner jobs list`"
 description: List provisioner jobs
 ---
 
diff --git a/docs/reference/cli/provisioner_keys_create.md b/docs/reference/cli/provisioner/keys/create.md
similarity index 95%
rename from docs/reference/cli/provisioner_keys_create.md
rename to docs/reference/cli/provisioner/keys/create.md
index 784c7057f6..5289e865f8 100644
--- a/docs/reference/cli/provisioner_keys_create.md
+++ b/docs/reference/cli/provisioner/keys/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner keys create
+title: "`coder provisioner keys create`"
 description: Create a new provisioner key
 ---
 
diff --git a/docs/reference/cli/provisioner_keys_delete.md b/docs/reference/cli/provisioner/keys/delete.md
similarity index 94%
rename from docs/reference/cli/provisioner_keys_delete.md
rename to docs/reference/cli/provisioner/keys/delete.md
index eba3c6a403..fe794be98a 100644
--- a/docs/reference/cli/provisioner_keys_delete.md
+++ b/docs/reference/cli/provisioner/keys/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner keys delete
+title: "`coder provisioner keys delete`"
 description: Delete a provisioner key
 ---
 
diff --git a/docs/reference/cli/provisioner/keys/index.md b/docs/reference/cli/provisioner/keys/index.md
new file mode 100644
index 0000000000..6a7ec3c025
--- /dev/null
+++ b/docs/reference/cli/provisioner/keys/index.md
@@ -0,0 +1,27 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder provisioner keys`"
+description: Manage provisioner keys
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage provisioner keys
+
+Aliases:
+
+* key
+
+## Usage
+
+```console
+coder provisioner keys
+```
+
+## Subcommands
+
+| Name                               | Purpose                                  |
+|------------------------------------|------------------------------------------|
+| [<code>create</code>](./create.md) | Create a new provisioner key             |
+| [<code>list</code>](./list.md)     | List provisioner keys in an organization |
+| [<code>delete</code>](./delete.md) | Delete a provisioner key                 |
diff --git a/docs/reference/cli/provisioner_keys_list.md b/docs/reference/cli/provisioner/keys/list.md
similarity index 96%
rename from docs/reference/cli/provisioner_keys_list.md
rename to docs/reference/cli/provisioner/keys/list.md
index db8a2d6d10..0ee8f7959b 100644
--- a/docs/reference/cli/provisioner_keys_list.md
+++ b/docs/reference/cli/provisioner/keys/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner keys list
+title: "`coder provisioner keys list`"
 description: List provisioner keys in an organization
 ---
 
diff --git a/docs/reference/cli/provisioner_list.md b/docs/reference/cli/provisioner/list.md
similarity index 99%
rename from docs/reference/cli/provisioner_list.md
rename to docs/reference/cli/provisioner/list.md
index b9cf2c06ea..e0052ca257 100644
--- a/docs/reference/cli/provisioner_list.md
+++ b/docs/reference/cli/provisioner/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner list
+title: "`coder provisioner list`"
 description: List provisioner daemons in an organization
 ---
 
diff --git a/docs/reference/cli/provisioner_start.md b/docs/reference/cli/provisioner/start.md
similarity index 99%
rename from docs/reference/cli/provisioner_start.md
rename to docs/reference/cli/provisioner/start.md
index 1e1bb58ae3..1dc89773a0 100644
--- a/docs/reference/cli/provisioner_start.md
+++ b/docs/reference/cli/provisioner/start.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: provisioner start
+title: "`coder provisioner start`"
 description: Run a provisioner daemon
 ---
 
diff --git a/docs/reference/cli/provisioner_jobs.md b/docs/reference/cli/provisioner_jobs.md
deleted file mode 100644
index 4d4193eddd..0000000000
--- a/docs/reference/cli/provisioner_jobs.md
+++ /dev/null
@@ -1,26 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: provisioner jobs
-description: View and manage provisioner jobs
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-View and manage provisioner jobs
-
-Aliases:
-
-* job
-
-## Usage
-
-```console
-coder provisioner jobs
-```
-
-## Subcommands
-
-| Name                                                | Purpose                  |
-|-----------------------------------------------------|--------------------------|
-| [<code>cancel</code>](./provisioner_jobs_cancel.md) | Cancel a provisioner job |
-| [<code>list</code>](./provisioner_jobs_list.md)     | List provisioner jobs    |
diff --git a/docs/reference/cli/provisioner_keys.md b/docs/reference/cli/provisioner_keys.md
deleted file mode 100644
index e886adf854..0000000000
--- a/docs/reference/cli/provisioner_keys.md
+++ /dev/null
@@ -1,27 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: provisioner keys
-description: Manage provisioner keys
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage provisioner keys
-
-Aliases:
-
-* key
-
-## Usage
-
-```console
-coder provisioner keys
-```
-
-## Subcommands
-
-| Name                                                | Purpose                                  |
-|-----------------------------------------------------|------------------------------------------|
-| [<code>create</code>](./provisioner_keys_create.md) | Create a new provisioner key             |
-| [<code>list</code>](./provisioner_keys_list.md)     | List provisioner keys in an organization |
-| [<code>delete</code>](./provisioner_keys_delete.md) | Delete a provisioner key                 |
diff --git a/docs/reference/cli/publickey.md b/docs/reference/cli/publickey.md
index 4a1b17060a..cd25a73182 100644
--- a/docs/reference/cli/publickey.md
+++ b/docs/reference/cli/publickey.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: publickey
+title: "`coder publickey`"
 description: Output your Coder public key used for Git operations
 ---
 
diff --git a/docs/reference/cli/rename.md b/docs/reference/cli/rename.md
index 1ae0133c2c..8a973464e6 100644
--- a/docs/reference/cli/rename.md
+++ b/docs/reference/cli/rename.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: rename
+title: "`coder rename`"
 description: Rename a workspace
 ---
 
diff --git a/docs/reference/cli/reset-password.md b/docs/reference/cli/reset-password.md
index 2a69dce4b6..b59892bd84 100644
--- a/docs/reference/cli/reset-password.md
+++ b/docs/reference/cli/reset-password.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: reset-password
+title: "`coder reset-password`"
 description: "Directly connect to the database to reset a user's password"
 ---
 
diff --git a/docs/reference/cli/restart.md b/docs/reference/cli/restart.md
index d55b3020d2..ce783d40f8 100644
--- a/docs/reference/cli/restart.md
+++ b/docs/reference/cli/restart.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: restart
+title: "`coder restart`"
 description: Restart a workspace
 ---
 
diff --git a/docs/reference/cli/schedule.md b/docs/reference/cli/schedule.md
deleted file mode 100644
index f4e8bfb267..0000000000
--- a/docs/reference/cli/schedule.md
+++ /dev/null
@@ -1,24 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: schedule
-description: Schedule automated start and stop times for workspaces
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Schedule automated start and stop times for workspaces
-
-## Usage
-
-```console
-coder schedule { show | start | stop | extend } <workspace>
-```
-
-## Subcommands
-
-| Name                                        | Purpose                                                         |
-|---------------------------------------------|-----------------------------------------------------------------|
-| [<code>show</code>](./schedule_show.md)     | Show workspace schedules                                        |
-| [<code>start</code>](./schedule_start.md)   | Edit workspace start schedule                                   |
-| [<code>stop</code>](./schedule_stop.md)     | Edit workspace stop schedule                                    |
-| [<code>extend</code>](./schedule_extend.md) | Extend the stop time of a currently running workspace instance. |
diff --git a/docs/reference/cli/schedule_extend.md b/docs/reference/cli/schedule/extend.md
similarity index 95%
rename from docs/reference/cli/schedule_extend.md
rename to docs/reference/cli/schedule/extend.md
index 6e91c9ceef..77b23d3652 100644
--- a/docs/reference/cli/schedule_extend.md
+++ b/docs/reference/cli/schedule/extend.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: schedule extend
+title: "`coder schedule extend`"
 description: Extend the stop time of a currently running workspace instance.
 ---
 
diff --git a/docs/reference/cli/schedule/index.md b/docs/reference/cli/schedule/index.md
new file mode 100644
index 0000000000..ea78ebcbe6
--- /dev/null
+++ b/docs/reference/cli/schedule/index.md
@@ -0,0 +1,24 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder schedule`"
+description: Schedule automated start and stop times for workspaces
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Schedule automated start and stop times for workspaces
+
+## Usage
+
+```console
+coder schedule { show | start | stop | extend } <workspace>
+```
+
+## Subcommands
+
+| Name                               | Purpose                                                         |
+|------------------------------------|-----------------------------------------------------------------|
+| [<code>show</code>](./show.md)     | Show workspace schedules                                        |
+| [<code>start</code>](./start.md)   | Edit workspace start schedule                                   |
+| [<code>stop</code>](./stop.md)     | Edit workspace stop schedule                                    |
+| [<code>extend</code>](./extend.md) | Extend the stop time of a currently running workspace instance. |
diff --git a/docs/reference/cli/schedule_show.md b/docs/reference/cli/schedule/show.md
similarity index 97%
rename from docs/reference/cli/schedule_show.md
rename to docs/reference/cli/schedule/show.md
index 2403794acd..72172ee904 100644
--- a/docs/reference/cli/schedule_show.md
+++ b/docs/reference/cli/schedule/show.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: schedule show
+title: "`coder schedule show`"
 description: Show workspace schedules
 ---
 
diff --git a/docs/reference/cli/schedule_start.md b/docs/reference/cli/schedule/start.md
similarity index 97%
rename from docs/reference/cli/schedule_start.md
rename to docs/reference/cli/schedule/start.md
index 66e70a6808..0d63f3ae2b 100644
--- a/docs/reference/cli/schedule_start.md
+++ b/docs/reference/cli/schedule/start.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: schedule start
+title: "`coder schedule start`"
 description: Edit workspace start schedule
 ---
 
diff --git a/docs/reference/cli/schedule_stop.md b/docs/reference/cli/schedule/stop.md
similarity index 96%
rename from docs/reference/cli/schedule_stop.md
rename to docs/reference/cli/schedule/stop.md
index 2a908b263d..fa40fb48ca 100644
--- a/docs/reference/cli/schedule_stop.md
+++ b/docs/reference/cli/schedule/stop.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: schedule stop
+title: "`coder schedule stop`"
 description: Edit workspace stop schedule
 ---
 
diff --git a/docs/reference/cli/secret.md b/docs/reference/cli/secret.md
deleted file mode 100644
index a8b64431ea..0000000000
--- a/docs/reference/cli/secret.md
+++ /dev/null
@@ -1,59 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: secret
-description: Manage secrets
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage secrets
-
-Aliases:
-
-* secrets
-
-## Usage
-
-```console
-coder secret
-```
-
-## Description
-
-```console
-  - Create a secret:
-
-     $ printf %s "$MYCLI_API_KEY" | coder secret create api-key --description "API key for workspace tools" --env API_KEY --file "~/.api-key"
-
-  - Update a secret:
-
-     $ echo -n "$NEW_SECRET_VALUE" | coder secret update api-key --description "Rotated API key" --env API_KEY --file "~/.api-key"
-
-  - Import secrets from a file:
-
-     $ coder secret import ./secrets.env
-
-  - List your secrets:
-
-     $ coder secret list
-
-  - Show a specific secret:
-
-     $ coder secret list api-key
-
-  - Delete a secret:
-
-     $ coder secret delete api-key
-```
-
-## Subcommands
-
-| Name                                        | Purpose                                           |
-|---------------------------------------------|---------------------------------------------------|
-| [<code>create</code>](./secret_create.md)   | Create a secret                                   |
-| [<code>update</code>](./secret_update.md)   | Update a secret                                   |
-| [<code>import</code>](./secret_import.md)   | Import secrets from a file                        |
-| [<code>enable</code>](./secret_enable.md)   | Enable a secret so it is injected into workspaces |
-| [<code>disable</code>](./secret_disable.md) | Disable a secret without removing it              |
-| [<code>list</code>](./secret_list.md)       | List secrets, or show one by name                 |
-| [<code>delete</code>](./secret_delete.md)   | Delete a secret                                   |
diff --git a/docs/reference/cli/secret_create.md b/docs/reference/cli/secret/create.md
similarity index 97%
rename from docs/reference/cli/secret_create.md
rename to docs/reference/cli/secret/create.md
index 9b4690e2e8..358be771dc 100644
--- a/docs/reference/cli/secret_create.md
+++ b/docs/reference/cli/secret/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret create
+title: "`coder secret create`"
 description: Create a secret
 ---
 
diff --git a/docs/reference/cli/secret_delete.md b/docs/reference/cli/secret/delete.md
similarity index 92%
rename from docs/reference/cli/secret_delete.md
rename to docs/reference/cli/secret/delete.md
index 7a9bc4f389..f2f05aef40 100644
--- a/docs/reference/cli/secret_delete.md
+++ b/docs/reference/cli/secret/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret delete
+title: "`coder secret delete`"
 description: Delete a secret
 ---
 
diff --git a/docs/reference/cli/secret_disable.md b/docs/reference/cli/secret/disable.md
similarity index 88%
rename from docs/reference/cli/secret_disable.md
rename to docs/reference/cli/secret/disable.md
index a20fb258df..04d03b40c4 100644
--- a/docs/reference/cli/secret_disable.md
+++ b/docs/reference/cli/secret/disable.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret disable
+title: "`coder secret disable`"
 description: Disable a secret without removing it
 ---
 
diff --git a/docs/reference/cli/secret_enable.md b/docs/reference/cli/secret/enable.md
similarity index 89%
rename from docs/reference/cli/secret_enable.md
rename to docs/reference/cli/secret/enable.md
index 82bc93bd5c..2c7283b224 100644
--- a/docs/reference/cli/secret_enable.md
+++ b/docs/reference/cli/secret/enable.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret enable
+title: "`coder secret enable`"
 description: Enable a secret so it is injected into workspaces
 ---
 
diff --git a/docs/reference/cli/secret_import.md b/docs/reference/cli/secret/import.md
similarity index 96%
rename from docs/reference/cli/secret_import.md
rename to docs/reference/cli/secret/import.md
index 809803ad14..91c79c9e07 100644
--- a/docs/reference/cli/secret_import.md
+++ b/docs/reference/cli/secret/import.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret import
+title: "`coder secret import`"
 description: Import secrets from a file
 ---
 
diff --git a/docs/reference/cli/secret/index.md b/docs/reference/cli/secret/index.md
new file mode 100644
index 0000000000..02c5bf4b09
--- /dev/null
+++ b/docs/reference/cli/secret/index.md
@@ -0,0 +1,59 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder secret`"
+description: Manage secrets
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage secrets
+
+Aliases:
+
+* secrets
+
+## Usage
+
+```console
+coder secret
+```
+
+## Description
+
+```console
+  - Create a secret:
+
+     $ printf %s "$MYCLI_API_KEY" | coder secret create api-key --description "API key for workspace tools" --env API_KEY --file "~/.api-key"
+
+  - Update a secret:
+
+     $ echo -n "$NEW_SECRET_VALUE" | coder secret update api-key --description "Rotated API key" --env API_KEY --file "~/.api-key"
+
+  - Import secrets from a file:
+
+     $ coder secret import ./secrets.env
+
+  - List your secrets:
+
+     $ coder secret list
+
+  - Show a specific secret:
+
+     $ coder secret list api-key
+
+  - Delete a secret:
+
+     $ coder secret delete api-key
+```
+
+## Subcommands
+
+| Name                                 | Purpose                                           |
+|--------------------------------------|---------------------------------------------------|
+| [<code>create</code>](./create.md)   | Create a secret                                   |
+| [<code>update</code>](./update.md)   | Update a secret                                   |
+| [<code>import</code>](./import.md)   | Import secrets from a file                        |
+| [<code>enable</code>](./enable.md)   | Enable a secret so it is injected into workspaces |
+| [<code>disable</code>](./disable.md) | Disable a secret without removing it              |
+| [<code>list</code>](./list.md)       | List secrets, or show one by name                 |
+| [<code>delete</code>](./delete.md)   | Delete a secret                                   |
diff --git a/docs/reference/cli/secret_list.md b/docs/reference/cli/secret/list.md
similarity index 96%
rename from docs/reference/cli/secret_list.md
rename to docs/reference/cli/secret/list.md
index dfb758ac60..8ddaae76d5 100644
--- a/docs/reference/cli/secret_list.md
+++ b/docs/reference/cli/secret/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret list
+title: "`coder secret list`"
 description: "List secrets, or show one by name"
 ---
 
diff --git a/docs/reference/cli/secret_update.md b/docs/reference/cli/secret/update.md
similarity index 97%
rename from docs/reference/cli/secret_update.md
rename to docs/reference/cli/secret/update.md
index c0485f9880..2f41553ff5 100644
--- a/docs/reference/cli/secret_update.md
+++ b/docs/reference/cli/secret/update.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: secret update
+title: "`coder secret update`"
 description: Update a secret
 ---
 
diff --git a/docs/reference/cli/server_create-admin-user.md b/docs/reference/cli/server/create-admin-user.md
similarity index 98%
rename from docs/reference/cli/server_create-admin-user.md
rename to docs/reference/cli/server/create-admin-user.md
index 2335e8b3ae..0049571ca3 100644
--- a/docs/reference/cli/server_create-admin-user.md
+++ b/docs/reference/cli/server/create-admin-user.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server create-admin-user
+title: "`coder server create-admin-user`"
 description: "Create a new admin user with the given username, email and password and adds it to every organization."
 ---
 
diff --git a/docs/reference/cli/server_dbcrypt_decrypt.md b/docs/reference/cli/server/dbcrypt/decrypt.md
similarity index 97%
rename from docs/reference/cli/server_dbcrypt_decrypt.md
rename to docs/reference/cli/server/dbcrypt/decrypt.md
index 3dafbbcc52..19cac2f8dc 100644
--- a/docs/reference/cli/server_dbcrypt_decrypt.md
+++ b/docs/reference/cli/server/dbcrypt/decrypt.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server dbcrypt decrypt
+title: "`coder server dbcrypt decrypt`"
 description: Decrypt a previously encrypted database.
 ---
 
diff --git a/docs/reference/cli/server_dbcrypt_delete.md b/docs/reference/cli/server/dbcrypt/delete.md
similarity index 96%
rename from docs/reference/cli/server_dbcrypt_delete.md
rename to docs/reference/cli/server/dbcrypt/delete.md
index 28030aa680..bdbd545108 100644
--- a/docs/reference/cli/server_dbcrypt_delete.md
+++ b/docs/reference/cli/server/dbcrypt/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server dbcrypt delete
+title: "`coder server dbcrypt delete`"
 description: Delete all encrypted data from the database. THIS IS A DESTRUCTIVE OPERATION.
 ---
 
diff --git a/docs/reference/cli/server/dbcrypt/index.md b/docs/reference/cli/server/dbcrypt/index.md
new file mode 100644
index 0000000000..73def9c5ba
--- /dev/null
+++ b/docs/reference/cli/server/dbcrypt/index.md
@@ -0,0 +1,23 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder server dbcrypt`"
+description: Manage database encryption.
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage database encryption.
+
+## Usage
+
+```console
+coder server dbcrypt
+```
+
+## Subcommands
+
+| Name                                 | Purpose                                                                       |
+|--------------------------------------|-------------------------------------------------------------------------------|
+| [<code>decrypt</code>](./decrypt.md) | Decrypt a previously encrypted database.                                      |
+| [<code>delete</code>](./delete.md)   | Delete all encrypted data from the database. THIS IS A DESTRUCTIVE OPERATION. |
+| [<code>rotate</code>](./rotate.md)   | Rotate database encryption keys.                                              |
diff --git a/docs/reference/cli/server_dbcrypt_rotate.md b/docs/reference/cli/server/dbcrypt/rotate.md
similarity index 97%
rename from docs/reference/cli/server_dbcrypt_rotate.md
rename to docs/reference/cli/server/dbcrypt/rotate.md
index 8cb058299e..ca2ae1aefa 100644
--- a/docs/reference/cli/server_dbcrypt_rotate.md
+++ b/docs/reference/cli/server/dbcrypt/rotate.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server dbcrypt rotate
+title: "`coder server dbcrypt rotate`"
 description: Rotate database encryption keys.
 ---
 
diff --git a/docs/reference/cli/server_fix-oidc-links.md b/docs/reference/cli/server/fix-oidc-links.md
similarity index 98%
rename from docs/reference/cli/server_fix-oidc-links.md
rename to docs/reference/cli/server/fix-oidc-links.md
index 40e47404ba..6974d96958 100644
--- a/docs/reference/cli/server_fix-oidc-links.md
+++ b/docs/reference/cli/server/fix-oidc-links.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server fix-oidc-links
+title: "`coder server fix-oidc-links`"
 description: "Reset OIDC linked IDs that do not match the expected issuer, allowing users to re-authenticate."
 ---
 
diff --git a/docs/reference/cli/server.md b/docs/reference/cli/server/index.md
similarity index 98%
rename from docs/reference/cli/server.md
rename to docs/reference/cli/server/index.md
index d899ca37ab..bafdae5588 100644
--- a/docs/reference/cli/server.md
+++ b/docs/reference/cli/server/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server
+title: "`coder server`"
 description: Start a Coder server
 ---
 
@@ -16,13 +16,13 @@ coder server [flags]
 
 ## Subcommands
 
-| Name                                                                      | Purpose                                                                                                |
-|---------------------------------------------------------------------------|--------------------------------------------------------------------------------------------------------|
-| [<code>create-admin-user</code>](./server_create-admin-user.md)           | Create a new admin user with the given username, email and password and adds it to every organization. |
-| [<code>postgres-builtin-url</code>](./server_postgres-builtin-url.md)     | Output the connection URL for the built-in PostgreSQL deployment.                                      |
-| [<code>postgres-builtin-serve</code>](./server_postgres-builtin-serve.md) | Run the built-in PostgreSQL deployment.                                                                |
-| [<code>fix-oidc-links</code>](./server_fix-oidc-links.md)                 | Reset OIDC linked IDs that do not match the expected issuer, allowing users to re-authenticate.        |
-| [<code>dbcrypt</code>](./server_dbcrypt.md)                               | Manage database encryption.                                                                            |
+| Name                                                               | Purpose                                                                                                |
+|--------------------------------------------------------------------|--------------------------------------------------------------------------------------------------------|
+| [<code>create-admin-user</code>](./create-admin-user.md)           | Create a new admin user with the given username, email and password and adds it to every organization. |
+| [<code>postgres-builtin-url</code>](./postgres-builtin-url.md)     | Output the connection URL for the built-in PostgreSQL deployment.                                      |
+| [<code>postgres-builtin-serve</code>](./postgres-builtin-serve.md) | Run the built-in PostgreSQL deployment.                                                                |
+| [<code>fix-oidc-links</code>](./fix-oidc-links.md)                 | Reset OIDC linked IDs that do not match the expected issuer, allowing users to re-authenticate.        |
+| [<code>dbcrypt</code>](./dbcrypt/index.md)                         | Manage database encryption.                                                                            |
 
 ## Options
 
diff --git a/docs/reference/cli/server_postgres-builtin-serve.md b/docs/reference/cli/server/postgres-builtin-serve.md
similarity index 90%
rename from docs/reference/cli/server_postgres-builtin-serve.md
rename to docs/reference/cli/server/postgres-builtin-serve.md
index c5f25976b2..9ae3477e96 100644
--- a/docs/reference/cli/server_postgres-builtin-serve.md
+++ b/docs/reference/cli/server/postgres-builtin-serve.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server postgres-builtin-serve
+title: "`coder server postgres-builtin-serve`"
 description: Run the built-in PostgreSQL deployment.
 ---
 
diff --git a/docs/reference/cli/server_postgres-builtin-url.md b/docs/reference/cli/server/postgres-builtin-url.md
similarity index 91%
rename from docs/reference/cli/server_postgres-builtin-url.md
rename to docs/reference/cli/server/postgres-builtin-url.md
index 52e5509055..a8ae5d9f04 100644
--- a/docs/reference/cli/server_postgres-builtin-url.md
+++ b/docs/reference/cli/server/postgres-builtin-url.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: server postgres-builtin-url
+title: "`coder server postgres-builtin-url`"
 description: Output the connection URL for the built-in PostgreSQL deployment.
 ---
 
diff --git a/docs/reference/cli/server_dbcrypt.md b/docs/reference/cli/server_dbcrypt.md
deleted file mode 100644
index 5a51200a47..0000000000
--- a/docs/reference/cli/server_dbcrypt.md
+++ /dev/null
@@ -1,23 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: server dbcrypt
-description: Manage database encryption.
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage database encryption.
-
-## Usage
-
-```console
-coder server dbcrypt
-```
-
-## Subcommands
-
-| Name                                                | Purpose                                                                       |
-|-----------------------------------------------------|-------------------------------------------------------------------------------|
-| [<code>decrypt</code>](./server_dbcrypt_decrypt.md) | Decrypt a previously encrypted database.                                      |
-| [<code>delete</code>](./server_dbcrypt_delete.md)   | Delete all encrypted data from the database. THIS IS A DESTRUCTIVE OPERATION. |
-| [<code>rotate</code>](./server_dbcrypt_rotate.md)   | Rotate database encryption keys.                                              |
diff --git a/docs/reference/cli/show.md b/docs/reference/cli/show.md
index 70c168ca96..2e9ef6cf3e 100644
--- a/docs/reference/cli/show.md
+++ b/docs/reference/cli/show.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: show
+title: "`coder show`"
 description: "Display details of a workspace's resources and agents"
 ---
 
diff --git a/docs/reference/cli/speedtest.md b/docs/reference/cli/speedtest.md
index f20ecdf699..3e4cf3c86b 100644
--- a/docs/reference/cli/speedtest.md
+++ b/docs/reference/cli/speedtest.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: speedtest
+title: "`coder speedtest`"
 description: Run upload and download tests from your machine to a workspace
 ---
 
diff --git a/docs/reference/cli/ssh.md b/docs/reference/cli/ssh.md
index fc9790f83b..7608cc16f1 100644
--- a/docs/reference/cli/ssh.md
+++ b/docs/reference/cli/ssh.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: ssh
+title: "`coder ssh`"
 description: Start a shell into a workspace or run a command
 ---
 
diff --git a/docs/reference/cli/start.md b/docs/reference/cli/start.md
index de7d9c882a..5d4308adc6 100644
--- a/docs/reference/cli/start.md
+++ b/docs/reference/cli/start.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: start
+title: "`coder start`"
 description: Start a workspace
 ---
 
diff --git a/docs/reference/cli/stat_cpu.md b/docs/reference/cli/stat/cpu.md
similarity index 95%
rename from docs/reference/cli/stat_cpu.md
rename to docs/reference/cli/stat/cpu.md
index a14844f59c..c2ba9536f6 100644
--- a/docs/reference/cli/stat_cpu.md
+++ b/docs/reference/cli/stat/cpu.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: stat cpu
+title: "`coder stat cpu`"
 description: "Show CPU usage, in cores."
 ---
 
diff --git a/docs/reference/cli/stat_disk.md b/docs/reference/cli/stat/disk.md
similarity index 96%
rename from docs/reference/cli/stat_disk.md
rename to docs/reference/cli/stat/disk.md
index 06d6fab19f..e54a98d4e5 100644
--- a/docs/reference/cli/stat_disk.md
+++ b/docs/reference/cli/stat/disk.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: stat disk
+title: "`coder stat disk`"
 description: "Show disk usage, in gigabytes."
 ---
 
diff --git a/docs/reference/cli/stat.md b/docs/reference/cli/stat/index.md
similarity index 69%
rename from docs/reference/cli/stat.md
rename to docs/reference/cli/stat/index.md
index b28a29d208..c3757b2e32 100644
--- a/docs/reference/cli/stat.md
+++ b/docs/reference/cli/stat/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: stat
+title: "`coder stat`"
 description: Show resource usage for the current workspace.
 ---
 
@@ -16,11 +16,11 @@ coder stat [flags]
 
 ## Subcommands
 
-| Name                                | Purpose                          |
-|-------------------------------------|----------------------------------|
-| [<code>cpu</code>](./stat_cpu.md)   | Show CPU usage, in cores.        |
-| [<code>mem</code>](./stat_mem.md)   | Show memory usage, in gigabytes. |
-| [<code>disk</code>](./stat_disk.md) | Show disk usage, in gigabytes.   |
+| Name                           | Purpose                          |
+|--------------------------------|----------------------------------|
+| [<code>cpu</code>](./cpu.md)   | Show CPU usage, in cores.        |
+| [<code>mem</code>](./mem.md)   | Show memory usage, in gigabytes. |
+| [<code>disk</code>](./disk.md) | Show disk usage, in gigabytes.   |
 
 ## Options
 
diff --git a/docs/reference/cli/stat_mem.md b/docs/reference/cli/stat/mem.md
similarity index 96%
rename from docs/reference/cli/stat_mem.md
rename to docs/reference/cli/stat/mem.md
index 04c8c65c99..5956aaa1da 100644
--- a/docs/reference/cli/stat_mem.md
+++ b/docs/reference/cli/stat/mem.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: stat mem
+title: "`coder stat mem`"
 description: "Show memory usage, in gigabytes."
 ---
 
diff --git a/docs/reference/cli/state.md b/docs/reference/cli/state.md
deleted file mode 100644
index 80c28d4e79..0000000000
--- a/docs/reference/cli/state.md
+++ /dev/null
@@ -1,22 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: state
-description: Manually manage Terraform state to fix broken workspaces
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manually manage Terraform state to fix broken workspaces
-
-## Usage
-
-```console
-coder state
-```
-
-## Subcommands
-
-| Name                                 | Purpose                                       |
-|--------------------------------------|-----------------------------------------------|
-| [<code>pull</code>](./state_pull.md) | Pull a Terraform state file from a workspace. |
-| [<code>push</code>](./state_push.md) | Push a Terraform state file to a workspace.   |
diff --git a/docs/reference/cli/state/index.md b/docs/reference/cli/state/index.md
new file mode 100644
index 0000000000..e2c400a2d5
--- /dev/null
+++ b/docs/reference/cli/state/index.md
@@ -0,0 +1,22 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder state`"
+description: Manually manage Terraform state to fix broken workspaces
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manually manage Terraform state to fix broken workspaces
+
+## Usage
+
+```console
+coder state
+```
+
+## Subcommands
+
+| Name                           | Purpose                                       |
+|--------------------------------|-----------------------------------------------|
+| [<code>pull</code>](./pull.md) | Pull a Terraform state file from a workspace. |
+| [<code>push</code>](./push.md) | Push a Terraform state file to a workspace.   |
diff --git a/docs/reference/cli/state_pull.md b/docs/reference/cli/state/pull.md
similarity index 94%
rename from docs/reference/cli/state_pull.md
rename to docs/reference/cli/state/pull.md
index 50ec4778bb..d0df970e02 100644
--- a/docs/reference/cli/state_pull.md
+++ b/docs/reference/cli/state/pull.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: state pull
+title: "`coder state pull`"
 description: Pull a Terraform state file from a workspace.
 ---
 
diff --git a/docs/reference/cli/state_push.md b/docs/reference/cli/state/push.md
similarity index 95%
rename from docs/reference/cli/state_push.md
rename to docs/reference/cli/state/push.md
index 620cea403e..dc30e96257 100644
--- a/docs/reference/cli/state_push.md
+++ b/docs/reference/cli/state/push.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: state push
+title: "`coder state push`"
 description: Push a Terraform state file to a workspace.
 ---
 
diff --git a/docs/reference/cli/stop.md b/docs/reference/cli/stop.md
index b07283846f..23680d0bb4 100644
--- a/docs/reference/cli/stop.md
+++ b/docs/reference/cli/stop.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: stop
+title: "`coder stop`"
 description: Stop a workspace
 ---
 
diff --git a/docs/reference/cli/support.md b/docs/reference/cli/support.md
deleted file mode 100644
index cc07633b2e..0000000000
--- a/docs/reference/cli/support.md
+++ /dev/null
@@ -1,21 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: support
-description: Commands for troubleshooting issues with a Coder deployment.
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Commands for troubleshooting issues with a Coder deployment.
-
-## Usage
-
-```console
-coder support
-```
-
-## Subcommands
-
-| Name                                       | Purpose                                                                     |
-|--------------------------------------------|-----------------------------------------------------------------------------|
-| [<code>bundle</code>](./support_bundle.md) | Generate a support bundle to troubleshoot issues connecting to a workspace. |
diff --git a/docs/reference/cli/support_bundle.md b/docs/reference/cli/support/bundle.md
similarity index 99%
rename from docs/reference/cli/support_bundle.md
rename to docs/reference/cli/support/bundle.md
index 2b03067543..491e8e2925 100644
--- a/docs/reference/cli/support_bundle.md
+++ b/docs/reference/cli/support/bundle.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: support bundle
+title: "`coder support bundle`"
 description: Generate a support bundle to troubleshoot issues connecting to a workspace.
 ---
 
diff --git a/docs/reference/cli/support/index.md b/docs/reference/cli/support/index.md
new file mode 100644
index 0000000000..e238af3c48
--- /dev/null
+++ b/docs/reference/cli/support/index.md
@@ -0,0 +1,21 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder support`"
+description: Commands for troubleshooting issues with a Coder deployment.
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Commands for troubleshooting issues with a Coder deployment.
+
+## Usage
+
+```console
+coder support
+```
+
+## Subcommands
+
+| Name                               | Purpose                                                                     |
+|------------------------------------|-----------------------------------------------------------------------------|
+| [<code>bundle</code>](./bundle.md) | Generate a support bundle to troubleshoot issues connecting to a workspace. |
diff --git a/docs/reference/cli/templates.md b/docs/reference/cli/templates.md
deleted file mode 100644
index 8ebaac9e16..0000000000
--- a/docs/reference/cli/templates.md
+++ /dev/null
@@ -1,44 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: templates
-description: Manage templates
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage templates
-
-Aliases:
-
-* template
-
-## Usage
-
-```console
-coder templates
-```
-
-## Description
-
-```console
-Templates are written in standard Terraform and describe the infrastructure for workspaces
-  - Create or push an update to the template. Your developers can update their
-workspaces:
-
-     $ coder templates push my-template
-```
-
-## Subcommands
-
-| Name                                             | Purpose                                                                          |
-|--------------------------------------------------|----------------------------------------------------------------------------------|
-| [<code>create</code>](./templates_create.md)     | DEPRECATED: Create a template from the current directory or as specified by flag |
-| [<code>edit</code>](./templates_edit.md)         | Edit the metadata of a template by name.                                         |
-| [<code>init</code>](./templates_init.md)         | Get started with a templated template.                                           |
-| [<code>list</code>](./templates_list.md)         | List all the templates available for the organization                            |
-| [<code>push</code>](./templates_push.md)         | Create or update a template from the current directory or as specified by flag   |
-| [<code>versions</code>](./templates_versions.md) | Manage different versions of the specified template                              |
-| [<code>presets</code>](./templates_presets.md)   | Manage presets of the specified template                                         |
-| [<code>delete</code>](./templates_delete.md)     | Delete templates                                                                 |
-| [<code>pull</code>](./templates_pull.md)         | Download the active, latest, or specified version of a template to a path.       |
-| [<code>archive</code>](./templates_archive.md)   | Archive unused or failed template versions from a given template(s)              |
diff --git a/docs/reference/cli/templates_archive.md b/docs/reference/cli/templates/archive.md
similarity index 96%
rename from docs/reference/cli/templates_archive.md
rename to docs/reference/cli/templates/archive.md
index 00b21fb85d..2612054105 100644
--- a/docs/reference/cli/templates_archive.md
+++ b/docs/reference/cli/templates/archive.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates archive
+title: "`coder templates archive`"
 description: "Archive unused or failed template versions from a given template(s)"
 ---
 
diff --git a/docs/reference/cli/templates_create.md b/docs/reference/cli/templates/create.md
similarity index 99%
rename from docs/reference/cli/templates_create.md
rename to docs/reference/cli/templates/create.md
index 1d9d26a922..4f7ae8b581 100644
--- a/docs/reference/cli/templates_create.md
+++ b/docs/reference/cli/templates/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates create
+title: "`coder templates create`"
 description: "DEPRECATED: Create a template from the current directory or as specified by flag"
 ---
 
diff --git a/docs/reference/cli/templates_delete.md b/docs/reference/cli/templates/delete.md
similarity index 94%
rename from docs/reference/cli/templates_delete.md
rename to docs/reference/cli/templates/delete.md
index 2467b55de9..8b6ad71b6a 100644
--- a/docs/reference/cli/templates_delete.md
+++ b/docs/reference/cli/templates/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates delete
+title: "`coder templates delete`"
 description: Delete templates
 ---
 
diff --git a/docs/reference/cli/templates_edit.md b/docs/reference/cli/templates/edit.md
similarity index 99%
rename from docs/reference/cli/templates_edit.md
rename to docs/reference/cli/templates/edit.md
index d294b5e1fc..43c3ae9577 100644
--- a/docs/reference/cli/templates_edit.md
+++ b/docs/reference/cli/templates/edit.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates edit
+title: "`coder templates edit`"
 description: Edit the metadata of a template by name.
 ---
 
diff --git a/docs/reference/cli/templates/index.md b/docs/reference/cli/templates/index.md
new file mode 100644
index 0000000000..6524b91f4f
--- /dev/null
+++ b/docs/reference/cli/templates/index.md
@@ -0,0 +1,44 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder templates`"
+description: Manage templates
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage templates
+
+Aliases:
+
+* template
+
+## Usage
+
+```console
+coder templates
+```
+
+## Description
+
+```console
+Templates are written in standard Terraform and describe the infrastructure for workspaces
+  - Create or push an update to the template. Your developers can update their
+workspaces:
+
+     $ coder templates push my-template
+```
+
+## Subcommands
+
+| Name                                         | Purpose                                                                          |
+|----------------------------------------------|----------------------------------------------------------------------------------|
+| [<code>create</code>](./create.md)           | DEPRECATED: Create a template from the current directory or as specified by flag |
+| [<code>edit</code>](./edit.md)               | Edit the metadata of a template by name.                                         |
+| [<code>init</code>](./init.md)               | Get started with a templated template.                                           |
+| [<code>list</code>](./list.md)               | List all the templates available for the organization                            |
+| [<code>push</code>](./push.md)               | Create or update a template from the current directory or as specified by flag   |
+| [<code>versions</code>](./versions/index.md) | Manage different versions of the specified template                              |
+| [<code>presets</code>](./presets/index.md)   | Manage presets of the specified template                                         |
+| [<code>delete</code>](./delete.md)           | Delete templates                                                                 |
+| [<code>pull</code>](./pull.md)               | Download the active, latest, or specified version of a template to a path.       |
+| [<code>archive</code>](./archive.md)         | Archive unused or failed template versions from a given template(s)              |
diff --git a/docs/reference/cli/templates_init.md b/docs/reference/cli/templates/init.md
similarity index 97%
rename from docs/reference/cli/templates_init.md
rename to docs/reference/cli/templates/init.md
index d7b88173f7..f53c463a12 100644
--- a/docs/reference/cli/templates_init.md
+++ b/docs/reference/cli/templates/init.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates init
+title: "`coder templates init`"
 description: Get started with a templated template.
 ---
 
diff --git a/docs/reference/cli/templates_list.md b/docs/reference/cli/templates/list.md
similarity index 97%
rename from docs/reference/cli/templates_list.md
rename to docs/reference/cli/templates/list.md
index 0f74cc4e6e..143391a973 100644
--- a/docs/reference/cli/templates_list.md
+++ b/docs/reference/cli/templates/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates list
+title: "`coder templates list`"
 description: List all the templates available for the organization
 ---
 
diff --git a/docs/reference/cli/templates_presets.md b/docs/reference/cli/templates/presets/index.md
similarity index 55%
rename from docs/reference/cli/templates_presets.md
rename to docs/reference/cli/templates/presets/index.md
index 327162f3d6..a7fb2c1440 100644
--- a/docs/reference/cli/templates_presets.md
+++ b/docs/reference/cli/templates/presets/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates presets
+title: "`coder templates presets`"
 description: Manage presets of the specified template
 ---
 
@@ -32,6 +32,6 @@ coder templates presets
 
 ## Subcommands
 
-| Name                                             | Purpose                                                                              |
-|--------------------------------------------------|--------------------------------------------------------------------------------------|
-| [<code>list</code>](./templates_presets_list.md) | List all presets of the specified template. Defaults to the active template version. |
+| Name                           | Purpose                                                                              |
+|--------------------------------|--------------------------------------------------------------------------------------|
+| [<code>list</code>](./list.md) | List all presets of the specified template. Defaults to the active template version. |
diff --git a/docs/reference/cli/templates_presets_list.md b/docs/reference/cli/templates/presets/list.md
similarity index 97%
rename from docs/reference/cli/templates_presets_list.md
rename to docs/reference/cli/templates/presets/list.md
index 0f2ecd3ff8..93cd4cf3ca 100644
--- a/docs/reference/cli/templates_presets_list.md
+++ b/docs/reference/cli/templates/presets/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates presets list
+title: "`coder templates presets list`"
 description: List all presets of the specified template. Defaults to the active template version.
 ---
 
diff --git a/docs/reference/cli/templates_pull.md b/docs/reference/cli/templates/pull.md
similarity index 97%
rename from docs/reference/cli/templates_pull.md
rename to docs/reference/cli/templates/pull.md
index e0d6d88ec9..a5aa1575c7 100644
--- a/docs/reference/cli/templates_pull.md
+++ b/docs/reference/cli/templates/pull.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates pull
+title: "`coder templates pull`"
 description: "Download the active, latest, or specified version of a template to a path."
 ---
 
diff --git a/docs/reference/cli/templates_push.md b/docs/reference/cli/templates/push.md
similarity index 99%
rename from docs/reference/cli/templates_push.md
rename to docs/reference/cli/templates/push.md
index 7ea0961889..95779c369e 100644
--- a/docs/reference/cli/templates_push.md
+++ b/docs/reference/cli/templates/push.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates push
+title: "`coder templates push`"
 description: Create or update a template from the current directory or as specified by flag
 ---
 
diff --git a/docs/reference/cli/templates_versions_archive.md b/docs/reference/cli/templates/versions/archive.md
similarity index 94%
rename from docs/reference/cli/templates_versions_archive.md
rename to docs/reference/cli/templates/versions/archive.md
index e216ce6c42..dd82edd1f1 100644
--- a/docs/reference/cli/templates_versions_archive.md
+++ b/docs/reference/cli/templates/versions/archive.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates versions archive
+title: "`coder templates versions archive`"
 description: "Archive a template version(s)."
 ---
 
diff --git a/docs/reference/cli/templates/versions/index.md b/docs/reference/cli/templates/versions/index.md
new file mode 100644
index 0000000000..87b6cc2403
--- /dev/null
+++ b/docs/reference/cli/templates/versions/index.md
@@ -0,0 +1,36 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder templates versions`"
+description: Manage different versions of the specified template
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage different versions of the specified template
+
+Aliases:
+
+* version
+
+## Usage
+
+```console
+coder templates versions
+```
+
+## Description
+
+```console
+  - List versions of a specific template:
+
+     $ coder templates versions list my-template
+```
+
+## Subcommands
+
+| Name                                     | Purpose                                         |
+|------------------------------------------|-------------------------------------------------|
+| [<code>list</code>](./list.md)           | List all the versions of the specified template |
+| [<code>archive</code>](./archive.md)     | Archive a template version(s).                  |
+| [<code>unarchive</code>](./unarchive.md) | Unarchive a template version(s).                |
+| [<code>promote</code>](./promote.md)     | Promote a template version to active.           |
diff --git a/docs/reference/cli/templates_versions_list.md b/docs/reference/cli/templates/versions/list.md
similarity index 96%
rename from docs/reference/cli/templates_versions_list.md
rename to docs/reference/cli/templates/versions/list.md
index 31039279a4..b769520e81 100644
--- a/docs/reference/cli/templates_versions_list.md
+++ b/docs/reference/cli/templates/versions/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates versions list
+title: "`coder templates versions list`"
 description: List all the versions of the specified template
 ---
 
diff --git a/docs/reference/cli/templates_versions_promote.md b/docs/reference/cli/templates/versions/promote.md
similarity index 96%
rename from docs/reference/cli/templates_versions_promote.md
rename to docs/reference/cli/templates/versions/promote.md
index 6e6ef6d216..405b161666 100644
--- a/docs/reference/cli/templates_versions_promote.md
+++ b/docs/reference/cli/templates/versions/promote.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates versions promote
+title: "`coder templates versions promote`"
 description: Promote a template version to active.
 ---
 
diff --git a/docs/reference/cli/templates_versions_unarchive.md b/docs/reference/cli/templates/versions/unarchive.md
similarity index 93%
rename from docs/reference/cli/templates_versions_unarchive.md
rename to docs/reference/cli/templates/versions/unarchive.md
index 8919dded8d..cff917344f 100644
--- a/docs/reference/cli/templates_versions_unarchive.md
+++ b/docs/reference/cli/templates/versions/unarchive.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: templates versions unarchive
+title: "`coder templates versions unarchive`"
 description: "Unarchive a template version(s)."
 ---
 
diff --git a/docs/reference/cli/templates_versions.md b/docs/reference/cli/templates_versions.md
deleted file mode 100644
index 099a48366e..0000000000
--- a/docs/reference/cli/templates_versions.md
+++ /dev/null
@@ -1,36 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: templates versions
-description: Manage different versions of the specified template
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage different versions of the specified template
-
-Aliases:
-
-* version
-
-## Usage
-
-```console
-coder templates versions
-```
-
-## Description
-
-```console
-  - List versions of a specific template:
-
-     $ coder templates versions list my-template
-```
-
-## Subcommands
-
-| Name                                                        | Purpose                                         |
-|-------------------------------------------------------------|-------------------------------------------------|
-| [<code>list</code>](./templates_versions_list.md)           | List all the versions of the specified template |
-| [<code>archive</code>](./templates_versions_archive.md)     | Archive a template version(s).                  |
-| [<code>unarchive</code>](./templates_versions_unarchive.md) | Unarchive a template version(s).                |
-| [<code>promote</code>](./templates_versions_promote.md)     | Promote a template version to active.           |
diff --git a/docs/reference/cli/tokens_create.md b/docs/reference/cli/tokens/create.md
similarity index 97%
rename from docs/reference/cli/tokens_create.md
rename to docs/reference/cli/tokens/create.md
index 6800e1ceca..24db897ff2 100644
--- a/docs/reference/cli/tokens_create.md
+++ b/docs/reference/cli/tokens/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: tokens create
+title: "`coder tokens create`"
 description: Create a token
 ---
 
diff --git a/docs/reference/cli/tokens.md b/docs/reference/cli/tokens/index.md
similarity index 52%
rename from docs/reference/cli/tokens.md
rename to docs/reference/cli/tokens/index.md
index ddd1f5d293..b53e6789ed 100644
--- a/docs/reference/cli/tokens.md
+++ b/docs/reference/cli/tokens/index.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: tokens
+title: "`coder tokens`"
 description: Manage personal access tokens
 ---
 
@@ -41,9 +41,9 @@ Tokens are used to authenticate automated clients to Coder.
 
 ## Subcommands
 
-| Name                                      | Purpose                                    |
-|-------------------------------------------|--------------------------------------------|
-| [<code>create</code>](./tokens_create.md) | Create a token                             |
-| [<code>list</code>](./tokens_list.md)     | List tokens                                |
-| [<code>view</code>](./tokens_view.md)     | Display detailed information about a token |
-| [<code>remove</code>](./tokens_remove.md) | Expire or delete a token                   |
+| Name                               | Purpose                                    |
+|------------------------------------|--------------------------------------------|
+| [<code>create</code>](./create.md) | Create a token                             |
+| [<code>list</code>](./list.md)     | List tokens                                |
+| [<code>view</code>](./view.md)     | Display detailed information about a token |
+| [<code>remove</code>](./remove.md) | Expire or delete a token                   |
diff --git a/docs/reference/cli/tokens_list.md b/docs/reference/cli/tokens/list.md
similarity index 97%
rename from docs/reference/cli/tokens_list.md
rename to docs/reference/cli/tokens/list.md
index b4860a2a0a..715b33cdc5 100644
--- a/docs/reference/cli/tokens_list.md
+++ b/docs/reference/cli/tokens/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: tokens list
+title: "`coder tokens list`"
 description: List tokens
 ---
 
diff --git a/docs/reference/cli/tokens_remove.md b/docs/reference/cli/tokens/remove.md
similarity index 94%
rename from docs/reference/cli/tokens_remove.md
rename to docs/reference/cli/tokens/remove.md
index a8b2c7f486..30c740510b 100644
--- a/docs/reference/cli/tokens_remove.md
+++ b/docs/reference/cli/tokens/remove.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: tokens remove
+title: "`coder tokens remove`"
 description: Expire or delete a token
 ---
 
diff --git a/docs/reference/cli/tokens_view.md b/docs/reference/cli/tokens/view.md
similarity index 96%
rename from docs/reference/cli/tokens_view.md
rename to docs/reference/cli/tokens/view.md
index 80cbd61c4e..02f0a9e193 100644
--- a/docs/reference/cli/tokens_view.md
+++ b/docs/reference/cli/tokens/view.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: tokens view
+title: "`coder tokens view`"
 description: Display detailed information about a token
 ---
 
diff --git a/docs/reference/cli/unfavorite.md b/docs/reference/cli/unfavorite.md
index 5ea98588d7..8ce8ceca5d 100644
--- a/docs/reference/cli/unfavorite.md
+++ b/docs/reference/cli/unfavorite.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: unfavorite
+title: "`coder unfavorite`"
 description: Remove a workspace from your favorites
 ---
 
diff --git a/docs/reference/cli/update.md b/docs/reference/cli/update.md
index efa9929651..d7c43c64d7 100644
--- a/docs/reference/cli/update.md
+++ b/docs/reference/cli/update.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: update
+title: "`coder update`"
 description: "Will update and start a given workspace if it is out of date. If the workspace is already running, it will be stopped first."
 ---
 
diff --git a/docs/reference/cli/users.md b/docs/reference/cli/users.md
deleted file mode 100644
index 85fd86c4a4..0000000000
--- a/docs/reference/cli/users.md
+++ /dev/null
@@ -1,32 +0,0 @@
----
-# Code generated by make gen. DO NOT EDIT.
-title: users
-description: Manage users
----
-
-<!-- DO NOT EDIT | GENERATED CONTENT -->
-
-Manage users
-
-Aliases:
-
-* user
-
-## Usage
-
-```console
-coder users [subcommand]
-```
-
-## Subcommands
-
-| Name                                               | Purpose                                                                               |
-|----------------------------------------------------|---------------------------------------------------------------------------------------|
-| [<code>create</code>](./users_create.md)           | Create a new user.                                                                    |
-| [<code>list</code>](./users_list.md)               | Prints the list of users.                                                             |
-| [<code>show</code>](./users_show.md)               | Show a single user. Use 'me' to indicate the currently authenticated user.            |
-| [<code>delete</code>](./users_delete.md)           | Delete a user by username or user_id.                                                 |
-| [<code>edit-roles</code>](./users_edit-roles.md)   | Edit a user's roles by username or id                                                 |
-| [<code>oidc-claims</code>](./users_oidc-claims.md) | Display the OIDC claims for the authenticated user.                                   |
-| [<code>activate</code>](./users_activate.md)       | Update a user's status to 'active'. Active users can fully interact with the platform |
-| [<code>suspend</code>](./users_suspend.md)         | Update a user's status to 'suspended'. A suspended user cannot log into the platform  |
diff --git a/docs/reference/cli/users_activate.md b/docs/reference/cli/users/activate.md
similarity index 96%
rename from docs/reference/cli/users_activate.md
rename to docs/reference/cli/users/activate.md
index ebee012268..7909cdb055 100644
--- a/docs/reference/cli/users_activate.md
+++ b/docs/reference/cli/users/activate.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users activate
+title: "`coder users activate`"
 description: "Update a user's status to 'active'. Active users can fully interact with the platform"
 ---
 
diff --git a/docs/reference/cli/users_create.md b/docs/reference/cli/users/create.md
similarity index 98%
rename from docs/reference/cli/users_create.md
rename to docs/reference/cli/users/create.md
index fa7560085f..b53cb609ba 100644
--- a/docs/reference/cli/users_create.md
+++ b/docs/reference/cli/users/create.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users create
+title: "`coder users create`"
 description: Create a new user.
 ---
 
diff --git a/docs/reference/cli/users_delete.md b/docs/reference/cli/users/delete.md
similarity index 89%
rename from docs/reference/cli/users_delete.md
rename to docs/reference/cli/users/delete.md
index 6b890c3967..ad95b96c28 100644
--- a/docs/reference/cli/users_delete.md
+++ b/docs/reference/cli/users/delete.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users delete
+title: "`coder users delete`"
 description: Delete a user by username or user_id.
 ---
 
diff --git a/docs/reference/cli/users_edit-roles.md b/docs/reference/cli/users/edit-roles.md
similarity index 94%
rename from docs/reference/cli/users_edit-roles.md
rename to docs/reference/cli/users/edit-roles.md
index 47383add42..423fd43f98 100644
--- a/docs/reference/cli/users_edit-roles.md
+++ b/docs/reference/cli/users/edit-roles.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users edit-roles
+title: "`coder users edit-roles`"
 description: "Edit a user's roles by username or id"
 ---
 
diff --git a/docs/reference/cli/users/index.md b/docs/reference/cli/users/index.md
new file mode 100644
index 0000000000..7f16508406
--- /dev/null
+++ b/docs/reference/cli/users/index.md
@@ -0,0 +1,32 @@
+---
+# Code generated by make gen. DO NOT EDIT.
+title: "`coder users`"
+description: Manage users
+---
+
+<!-- DO NOT EDIT | GENERATED CONTENT -->
+
+Manage users
+
+Aliases:
+
+* user
+
+## Usage
+
+```console
+coder users [subcommand]
+```
+
+## Subcommands
+
+| Name                                         | Purpose                                                                               |
+|----------------------------------------------|---------------------------------------------------------------------------------------|
+| [<code>create</code>](./create.md)           | Create a new user.                                                                    |
+| [<code>list</code>](./list.md)               | Prints the list of users.                                                             |
+| [<code>show</code>](./show.md)               | Show a single user. Use 'me' to indicate the currently authenticated user.            |
+| [<code>delete</code>](./delete.md)           | Delete a user by username or user_id.                                                 |
+| [<code>edit-roles</code>](./edit-roles.md)   | Edit a user's roles by username or id                                                 |
+| [<code>oidc-claims</code>](./oidc-claims.md) | Display the OIDC claims for the authenticated user.                                   |
+| [<code>activate</code>](./activate.md)       | Update a user's status to 'active'. Active users can fully interact with the platform |
+| [<code>suspend</code>](./suspend.md)         | Update a user's status to 'suspended'. A suspended user cannot log into the platform  |
diff --git a/docs/reference/cli/users_list.md b/docs/reference/cli/users/list.md
similarity index 97%
rename from docs/reference/cli/users_list.md
rename to docs/reference/cli/users/list.md
index a9e2955098..60d131ae89 100644
--- a/docs/reference/cli/users_list.md
+++ b/docs/reference/cli/users/list.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users list
+title: "`coder users list`"
 description: Prints the list of users.
 ---
 
diff --git a/docs/reference/cli/users_oidc-claims.md b/docs/reference/cli/users/oidc-claims.md
similarity index 96%
rename from docs/reference/cli/users_oidc-claims.md
rename to docs/reference/cli/users/oidc-claims.md
index 396e2f76f4..28fcfaeb92 100644
--- a/docs/reference/cli/users_oidc-claims.md
+++ b/docs/reference/cli/users/oidc-claims.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users oidc-claims
+title: "`coder users oidc-claims`"
 description: Display the OIDC claims for the authenticated user.
 ---
 
diff --git a/docs/reference/cli/users_show.md b/docs/reference/cli/users/show.md
similarity index 95%
rename from docs/reference/cli/users_show.md
rename to docs/reference/cli/users/show.md
index f4b92ac594..8739eb6d62 100644
--- a/docs/reference/cli/users_show.md
+++ b/docs/reference/cli/users/show.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users show
+title: "`coder users show`"
 description: "Show a single user. Use 'me' to indicate the currently authenticated user."
 ---
 
diff --git a/docs/reference/cli/users_suspend.md b/docs/reference/cli/users/suspend.md
similarity index 96%
rename from docs/reference/cli/users_suspend.md
rename to docs/reference/cli/users/suspend.md
index efb26bd148..421122d60f 100644
--- a/docs/reference/cli/users_suspend.md
+++ b/docs/reference/cli/users/suspend.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: users suspend
+title: "`coder users suspend`"
 description: "Update a user's status to 'suspended'. A suspended user cannot log into the platform"
 ---
 
diff --git a/docs/reference/cli/version.md b/docs/reference/cli/version.md
index 19ff4808e7..c2eab51bad 100644
--- a/docs/reference/cli/version.md
+++ b/docs/reference/cli/version.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: version
+title: "`coder version`"
 description: Show coder version
 ---
 
diff --git a/docs/reference/cli/whoami.md b/docs/reference/cli/whoami.md
index d1db41b119..1209d6c292 100644
--- a/docs/reference/cli/whoami.md
+++ b/docs/reference/cli/whoami.md
@@ -1,6 +1,6 @@
 ---
 # Code generated by make gen. DO NOT EDIT.
-title: whoami
+title: "`coder whoami`"
 description: Fetch authenticated user info for Coder deployment
 ---
 
diff --git a/docs/reference/glossary.md b/docs/reference/glossary.md
index 1b6ba63995..e65e8b5413 100644
--- a/docs/reference/glossary.md
+++ b/docs/reference/glossary.md
@@ -143,7 +143,7 @@ Refer to [About Coder](../README.md#coder-workspaces).
 
 The CLI command that starts [`coderd`](#coderd).
 Use this name only for the command a reader runs, not as a name for the [control plane](#control-plane) itself.
-Refer to the [`coder server` reference](./cli/server.md).
+Refer to the [`coder server` reference](./cli/server/index.md).
 
 ### `coder_agent`
 
diff --git a/docs/reference/index.md b/docs/reference/index.md
index 2512eac13c..aec139c02e 100644
--- a/docs/reference/index.md
+++ b/docs/reference/index.md
@@ -39,7 +39,7 @@ curl https://coder.example.com/api/v2/workspaces?q=owner:me \
 
 We publish an [API reference](../reference/api/index.md) in our documentation.
 You can also enable a
-[Swagger endpoint](../reference/cli/server.md#--swagger-enable) on your Coder
+[Swagger endpoint](../reference/cli/server/index.md#--swagger-enable) on your Coder
 deployment.
 
 ## Use cases
diff --git a/docs/support/support-bundle.md b/docs/support/support-bundle.md
index 2b97e4c2c3..41b3812588 100644
--- a/docs/support/support-bundle.md
+++ b/docs/support/support-bundle.md
@@ -45,7 +45,7 @@ A brief overview of all files contained in the bundle is provided below:
 | `cli_logs.txt`                                | Logs from running the `coder support bundle` command.                                                                                                                                  |
 | `deployment/buildinfo.json`                   | Coder version and build information.                                                                                                                                                   |
 | `deployment/config.json`                      | Deployment [configuration](../reference/api/general.md#get-deployment-config), with secret values removed. *Requires Owner role.*                                                      |
-| `deployment/experiments.json`                 | Any [experiments](../reference/cli/server.md#--experiments) currently enabled for the deployment.                                                                                      |
+| `deployment/experiments.json`                 | Any [experiments](../reference/cli/server/index.md#--experiments) currently enabled for the deployment.                                                                                |
 | `deployment/health.json`                      | A snapshot of the [health status](../admin/monitoring/health-check.md) of the deployment. *Requires Owner role.*                                                                       |
 | `logs.txt`                                    | Logs from the `codersdk.Client` used to generate the bundle.                                                                                                                           |
 | `network/connection_info.json`                | Information used by workspace agents used to connect to Coder (DERP map etc.)                                                                                                          |
@@ -72,7 +72,7 @@ A brief overview of all files contained in the bundle is provided below:
    > It is recommended to generate a support bundle from a location
    > experiencing workspace connectivity issues.
 
-3. Ensure you are [logged in](../reference/cli/login.md) to your Coder
+3. Ensure you are [logged in](../reference/cli/login/index.md) to your Coder
    deployment. Any authenticated user can generate a support bundle. Users with
    the Owner role will get the most complete bundle; non-admin users will still
    get a useful bundle but some admin-only data will be omitted (see the note
diff --git a/docs/tutorials/best-practices/organizations.md b/docs/tutorials/best-practices/organizations.md
index 525d38c284..8490af9a43 100644
--- a/docs/tutorials/best-practices/organizations.md
+++ b/docs/tutorials/best-practices/organizations.md
@@ -62,7 +62,7 @@ use organizations for several use cases.
 Since templates and workspaces cannot be moved nor can they belong to multiple
 organizations, we recommend that you deprecate your template
 [through the API](../../reference/api/templates.md#update-template-settings-by-id)
-or [through the Coder CLI](../../reference/cli/templates_edit.md#--deprecated).
+or [through the Coder CLI](../../reference/cli/templates/edit.md#--deprecated).
 When a template is deprecated, the admin prevents new workspaces from being
 created and developers are notified with a deprecation message which can link to
 an external wiki page on migration instructions.
diff --git a/docs/tutorials/best-practices/security-best-practices.md b/docs/tutorials/best-practices/security-best-practices.md
index 9386c80640..fbdf1b610e 100644
--- a/docs/tutorials/best-practices/security-best-practices.md
+++ b/docs/tutorials/best-practices/security-best-practices.md
@@ -45,10 +45,10 @@ are automatically up to date.
 ### Encryption in transit
 
 Place Coder behind a TLS-capable reverse-proxy/load balancer and enable
-[Strict Transport Security](../../reference/cli/server.md#--strict-transport-security)
+[Strict Transport Security](../../reference/cli/server/index.md#--strict-transport-security)
 so that connections from end users are always encrypted.
 
-Enable [TLS](../../reference/cli/server.md#--tls-address) on the control plane and
+Enable [TLS](../../reference/cli/server/index.md#--tls-address) on the control plane and
 encrypt traffic from the reverse-proxy/load balancer to the control plane, so that
 even if an attacker gains access to your network, they will not be able to snoop
 on control plane traffic.
@@ -123,7 +123,7 @@ of the Coder deployment.
 ### Encryption in transit
 
 Enable TLS on PostgreSQL and set `sslmode=verify-full` in your
-[postgres URL](../../reference/cli/server.md#--postgres-url) on the control plane.
+[postgres URL](../../reference/cli/server/index.md#--postgres-url) on the control plane.
 This configures the control plane to only establish TLS connections to PostgreSQL and
 check that the PostgreSQL server’s certificate is valid and matches the expected
 hostname.
@@ -492,7 +492,7 @@ public STUN servers.
 You may choose not to configure any STUN servers, in which case most workspace
 traffic will need to be relayed via DERP. You may choose to deploy your own STUN
 servers, either on the public Internet, or on your corporate network and
-[configure Coder to use it](../../reference/cli/server.md#--derp-server-stun-addresses).
+[configure Coder to use it](../../reference/cli/server/index.md#--derp-server-stun-addresses).
 
 If you do not consider the addresses and ports to be sensitive, we recommend
 using the default set of STUN servers operated by Google.
@@ -502,7 +502,7 @@ using the default set of STUN servers operated by Google.
 Coder workspace apps are a way to allow users to access web applications running
 in the workspace via the control plane or Workspace Proxy.
 
-1. [Disable workspace apps on sub-paths](../../reference/cli/server.md#--disable-path-apps)
+1. [Disable workspace apps on sub-paths](../../reference/cli/server/index.md#--disable-path-apps)
    of the main Coder domain name.
 
 1. [Use a separate, wildcard domain name](../../admin/setup/index.md#wildcard-access-url)
diff --git a/docs/tutorials/best-practices/speed-up-templates.md b/docs/tutorials/best-practices/speed-up-templates.md
index b7019d61bf..ea7853aa0f 100644
--- a/docs/tutorials/best-practices/speed-up-templates.md
+++ b/docs/tutorials/best-practices/speed-up-templates.md
@@ -68,7 +68,7 @@ Coder installation.
 
 `coder server` by default provides three built-in provisioner daemons
 (controlled by the
-[`CODER_PROVISIONER_DAEMONS`](../../reference/cli/server.md#--provisioner-daemons)
+[`CODER_PROVISIONER_DAEMONS`](../../reference/cli/server/index.md#--provisioner-daemons)
 config option). Each provisioner daemon can handle one single job (such as
 start, stop, or delete) at a time and can be resource intensive. When all
 provisioners are busy, workspaces enter a "pending" state until a provisioner
@@ -79,7 +79,7 @@ becomes available.
 Provisioners are queue-based to reduce unpredictable load to the control plane.
 If you require a higher bandwidth of provisioner jobs, you can do so by
 increasing the
-[`CODER_PROVISIONER_DAEMONS`](../../reference/cli/server.md#--provisioner-daemons)
+[`CODER_PROVISIONER_DAEMONS`](../../reference/cli/server/index.md#--provisioner-daemons)
 config option.
 
 You risk overloading Coder if you use too many built-in provisioners, so we
@@ -90,7 +90,7 @@ than five provisioners, we recommend that you move to
 `coderd` replicas.
 
 Visit the
-[CLI documentation](../../reference/cli/server.md#--provisioner-daemons) for
+[CLI documentation](../../reference/cli/server/index.md#--provisioner-daemons) for
 more information about increasing provisioner daemons, configuring external
 provisioners, and other options.
 
@@ -162,7 +162,7 @@ provider versions.
 ### Cache directory
 
 Coder will instruct Terraform to cache its downloaded providers in the
-configured [`CODER_CACHE_DIRECTORY`](../../reference/cli/server.md#--cache-dir)
+configured [`CODER_CACHE_DIRECTORY`](../../reference/cli/server/index.md#--cache-dir)
 directory.
 
 Ensure that this directory is set to a location on disk which will persist
diff --git a/docs/tutorials/faqs.md b/docs/tutorials/faqs.md
index aaa0f6276e..8f5f977f2c 100644
--- a/docs/tutorials/faqs.md
+++ b/docs/tutorials/faqs.md
@@ -90,11 +90,11 @@ to establish these direct connections.
 Setting the following flags as shown disables this logic to simplify
 troubleshooting.
 
-| Flag                                                                                          | Value       | Meaning                               |
-|-----------------------------------------------------------------------------------------------|-------------|---------------------------------------|
-| [`CODER_BLOCK_DIRECT`](../reference/cli/server.md#--block-direct-connections)                 | `true`      | Blocks direct connections             |
-| [`CODER_DERP_SERVER_STUN_ADDRESSES`](../reference/cli/server.md#--derp-server-stun-addresses) | `"disable"` | Disables STUN                         |
-| [`CODER_DERP_FORCE_WEBSOCKETS`](../reference/cli/server.md#--derp-force-websockets)           | `true`      | Forces websockets over Tailscale DERP |
+| Flag                                                                                                | Value       | Meaning                               |
+|-----------------------------------------------------------------------------------------------------|-------------|---------------------------------------|
+| [`CODER_BLOCK_DIRECT`](../reference/cli/server/index.md#--block-direct-connections)                 | `true`      | Blocks direct connections             |
+| [`CODER_DERP_SERVER_STUN_ADDRESSES`](../reference/cli/server/index.md#--derp-server-stun-addresses) | `"disable"` | Disables STUN                         |
+| [`CODER_DERP_FORCE_WEBSOCKETS`](../reference/cli/server/index.md#--derp-force-websockets)           | `true`      | Forces websockets over Tailscale DERP |
 
 ## How do I configure NGINX as the reverse proxy in front of Coder?
 
diff --git a/docs/user-guides/user-secrets.md b/docs/user-guides/user-secrets.md
index c919ac8581..a08394c0a9 100644
--- a/docs/user-guides/user-secrets.md
+++ b/docs/user-guides/user-secrets.md
@@ -237,7 +237,7 @@ coder secret import - --input-format yaml < ./secrets.yaml
 The import is all or nothing and never overwrites existing secrets. Keys that
 are valid environment variable names are injected under the same name; other
 keys are imported without an environment variable target. For details, see
-[`coder secret import`](../reference/cli/secret_import.md).
+[`coder secret import`](../reference/cli/secret/import.md).
 
 ### Create a disabled secret
 
@@ -345,5 +345,5 @@ variable or file target.
 To import secrets programmatically, use the
 [Secrets API](../reference/api/secrets.md#import-user-secrets-from-a-file).
 
-For full command details, see [`coder secret`](../reference/cli/secret.md) and
+For full command details, see [`coder secret`](../reference/cli/secret/index.md) and
 the [Secrets API reference](../reference/api/secrets.md).
diff --git a/scripts/clidocgen/command.tpl b/scripts/clidocgen/command.tpl
index c2ced269c7..f996dcc7d9 100644
--- a/scripts/clidocgen/command.tpl
+++ b/scripts/clidocgen/command.tpl
@@ -33,7 +33,7 @@ Aliases:
 | Name |   Purpose |
 | ---- |   ----- |
 {{- end }}
-| [{{ $cmd.Name | wrapCode }}](./{{commandURI $cmd}}) | {{ $cmd.Short }} |
+| [{{ $cmd.Name | wrapCode }}]({{ subcommandLink $cmd }}) | {{ $cmd.Short }} |
 {{- end}}
 {{ "" }}
 {{- range $index, $opt := visibleOptions . }}
diff --git a/scripts/clidocgen/gen.go b/scripts/clidocgen/gen.go
index fa30bdadcf..0a1243fa61 100644
--- a/scripts/clidocgen/gen.go
+++ b/scripts/clidocgen/gen.go
@@ -1,15 +1,19 @@
 package main
 
 import (
+	"cmp"
 	_ "embed"
 	"fmt"
 	"io"
 	"os"
+	"path"
 	"path/filepath"
+	"slices"
 	"strings"
 	"text/template"
 
 	"github.com/acarl005/stripansi"
+	"golang.org/x/xerrors"
 
 	"github.com/coder/coder/v2/buildinfo"
 	"github.com/coder/coder/v2/scripts/atomicwrite"
@@ -26,16 +30,7 @@ var commandTemplate *template.Template
 func init() {
 	commandTemplate = template.Must(
 		template.New("command.tpl").Funcs(template.FuncMap{
-			"visibleSubcommands": func(cmd *serpent.Command) []*serpent.Command {
-				var visible []*serpent.Command
-				for _, sub := range cmd.Children {
-					if sub.Hidden {
-						continue
-					}
-					visible = append(visible, sub)
-				}
-				return visible
-			},
+			"visibleSubcommands": visibleSubcommands,
 			"visibleOptions": func(cmd *serpent.Command) []serpent.Option {
 				var visible []serpent.Option
 				for _, opt := range cmd.Options {
@@ -57,7 +52,7 @@ func init() {
 			"wrapCode": func(s string) string {
 				return fmt.Sprintf("<code>%s</code>", s)
 			},
-			"commandURI": fmtDocFilename,
+			"subcommandLink": subcommandLink,
 			// frontMatter renders the page's YAML front matter through the
 			// shared docgenenv emitter, so the CLI and API generators cannot
 			// drift on field set, ordering, or escaping. The CLI index mirrors
@@ -95,24 +90,64 @@ func init() {
 	)
 }
 
-func fullName(cmd *serpent.Command) string {
-	if cmd.FullName() == "coder" {
-		return "coder"
+// visibleSubcommands returns cmd's direct subcommands that are not hidden.
+// Hidden commands (and their subtrees) get no reference page.
+func visibleSubcommands(cmd *serpent.Command) []*serpent.Command {
+	var visible []*serpent.Command
+	for _, sub := range cmd.Children {
+		if sub.Hidden {
+			continue
+		}
+		visible = append(visible, sub)
 	}
-	return strings.TrimPrefix(cmd.FullName(), "coder ")
+	return visible
+}
+
+// inlineCode wraps s in backticks. Docs renderers show a title that is
+// entirely wrapped in one pair of backticks as inline code.
+func inlineCode(s string) string {
+	return "`" + s + "`"
 }
 
 // cliCommandRoute maps a serpent command to the docgenenv.Route whose per-page
 // metadata the CLI generator mirrors into that command's page front matter.
-// main layers the manifest Path onto the same value when it rebuilds the nav
-// tree, so the per-command field mapping lives in exactly one place.
+// The page title is the full invocation (for example "`coder users list`"), so
+// the page reads as a command even though its sidebar entry only shows the
+// last verb (see cliManifestRoute).
 func cliCommandRoute(cmd *serpent.Command) docgenenv.Route {
 	return docgenenv.Route{
-		Title:       fullName(cmd),
+		Title:       inlineCode(cmd.FullName()),
 		Description: cmd.Short,
 	}
 }
 
+// cliManifestRoute builds the manifest nav entry for cmd and, recursively, its
+// visible subcommands, so the sidebar nests the same way the command tree
+// does. Each entry is titled with only its own verb (for example "`list`"
+// under "`users`") because its ancestors already appear above it in the nav.
+func cliManifestRoute(cmd *serpent.Command) docgenenv.Route {
+	return docgenenv.Route{
+		Title:       inlineCode(cmd.Name()),
+		Description: cmd.Short,
+		Path:        path.Join("reference/cli", fmtDocFilename(cmd)),
+		Children:    cliManifestChildren(cmd),
+	}
+}
+
+// cliManifestChildren returns the manifest entries for cmd's visible
+// subcommands, sorted by name so the output is deterministic.
+func cliManifestChildren(cmd *serpent.Command) []docgenenv.Route {
+	subs := visibleSubcommands(cmd)
+	slices.SortFunc(subs, func(a, b *serpent.Command) int {
+		return cmp.Compare(a.Name(), b.Name())
+	})
+	var children []docgenenv.Route
+	for _, sub := range subs {
+		children = append(children, cliManifestRoute(sub))
+	}
+	return children
+}
+
 // cliIndexRouteFrom returns the CLI index page's route: a copy of the "Command
 // Line" manifest route with its nav children dropped. Copying the whole route
 // instead of enumerating fields means the index front matter mirrors every
@@ -124,13 +159,32 @@ func cliIndexRouteFrom(cmdLine docgenenv.Route) docgenenv.Route {
 	return cmdLine
 }
 
+// fmtDocFilename returns the path of cmd's reference page relative to the CLI
+// reference directory. Pages nest by command path so the URL mirrors the
+// invocation: "coder users list" is users/list.md, and a command with visible
+// subcommands is the index.md of its own directory (users/index.md) so its
+// subcommands' pages sit beneath it.
 func fmtDocFilename(cmd *serpent.Command) string {
-	if cmd.FullName() == "coder" {
-		// Special case for index.
-		return "./index.md"
+	var parts []string
+	for c := cmd; c.Parent != nil; c = c.Parent {
+		parts = append([]string{c.Name()}, parts...)
 	}
-	name := strings.ReplaceAll(fullName(cmd), " ", "_")
-	return fmt.Sprintf("%s.md", name)
+	if len(parts) == 0 || len(visibleSubcommands(cmd)) > 0 {
+		return path.Join(append(parts, "index.md")...)
+	}
+	return path.Join(parts...) + ".md"
+}
+
+// subcommandLink returns the link from a parent command's page to sub's page.
+// A parent page is always the index.md of the directory its subcommands live
+// in, so the link is relative to that directory.
+func subcommandLink(sub *serpent.Command) string {
+	parentDir := path.Dir(fmtDocFilename(sub.Parent))
+	rel := fmtDocFilename(sub)
+	if parentDir != "." {
+		rel = strings.TrimPrefix(rel, parentDir+"/")
+	}
+	return "./" + rel
 }
 
 func writeCommand(w io.Writer, cmd *serpent.Command) error {
@@ -167,7 +221,10 @@ func genTree(dir string, cmd *serpent.Command, wroteLog map[string]*serpent.Comm
 		return nil
 	}
 
-	path := filepath.Join(dir, fmtDocFilename(cmd))
+	pagePath := filepath.Join(dir, filepath.FromSlash(fmtDocFilename(cmd)))
+	if err := os.MkdirAll(filepath.Dir(pagePath), 0o755); err != nil {
+		return xerrors.Errorf("create directory for %q: %w", pagePath, err)
+	}
 
 	var buf strings.Builder
 	err := writeCommand(&buf, cmd)
@@ -175,16 +232,16 @@ func genTree(dir string, cmd *serpent.Command, wroteLog map[string]*serpent.Comm
 		return err
 	}
 
-	err = atomicwrite.File(path, []byte(buf.String()))
+	err = atomicwrite.File(pagePath, []byte(buf.String()))
 	if err != nil {
 		return err
 	}
 
 	flog.Successf(
 		"wrote\t%s",
-		path,
+		pagePath,
 	)
-	wroteLog[path] = cmd
+	wroteLog[pagePath] = cmd
 	for _, sub := range cmd.Children {
 		err = genTree(dir, sub, wroteLog)
 		if err != nil {
diff --git a/scripts/clidocgen/main.go b/scripts/clidocgen/main.go
index 2fb698082e..4e91bafd1c 100644
--- a/scripts/clidocgen/main.go
+++ b/scripts/clidocgen/main.go
@@ -1,11 +1,10 @@
 package main
 
 import (
-	"cmp"
 	"encoding/json"
+	"flag"
 	"os"
 	"path/filepath"
-	"slices"
 
 	"github.com/coder/coder/v2/enterprise/cli"
 	"github.com/coder/coder/v2/scripts/atomicwrite"
@@ -44,6 +43,9 @@ func deleteEmptyDirs(dir string) error {
 }
 
 func main() {
+	manifestOnly := flag.Bool("manifest-only", false, "Only rebuild the \"Command Line\" section of manifest.json; do not write reference pages.")
+	flag.Parse()
+
 	docgenenv.Prepare()
 
 	workdir, err := os.Getwd()
@@ -52,9 +54,6 @@ func main() {
 	}
 	root := (&cli.RootCmd{})
 
-	// wroteMap indexes file paths to commands.
-	wroteMap := make(map[string]*serpent.Command)
-
 	var (
 		docsDir        = filepath.Join(workdir, "docs")
 		cliMarkdownDir = filepath.Join(docsDir, "reference/cli")
@@ -86,7 +85,33 @@ func main() {
 	if err != nil {
 		flog.Fatalf("creating command: %v", err)
 	}
-	err = genTree(
+	if !*manifestOnly {
+		writePages(cliMarkdownDir, cmd)
+	}
+
+	// Rebuild the "Command Line" route's children from the command tree so
+	// the nav nests the same way the generated pages do. cmdLine aliases the
+	// manifest loaded above, so mutating it updates the manifest in place.
+	cmdLine.Children = cliManifestChildren(cmd)
+
+	manifestByt, err := json.MarshalIndent(man, "", "  ")
+	if err != nil {
+		flog.Fatalf("marshaling manifest: %v", err)
+	}
+
+	err = atomicwrite.File(manifestPath, manifestByt)
+	if err != nil {
+		flog.Fatalf("writing manifest: %v", err)
+	}
+}
+
+// writePages generates a reference page for every visible command under
+// cliMarkdownDir, then deletes pages and directories left over from commands
+// that no longer exist.
+func writePages(cliMarkdownDir string, cmd *serpent.Command) {
+	// wroteMap indexes file paths to commands.
+	wroteMap := make(map[string]*serpent.Command)
+	err := genTree(
 		cliMarkdownDir,
 		cmd,
 		wroteMap,
@@ -120,32 +145,4 @@ func main() {
 	if err != nil {
 		flog.Fatalf("deleting empty dirs: %v", err)
 	}
-
-	// Rebuild the "Command Line" route's children from the generated pages.
-	// cmdLine aliases the manifest loaded above, so mutating it updates the
-	// manifest in place.
-	cmdLine.Children = nil
-	for path, cmd := range wroteMap {
-		relPath, err := filepath.Rel(docsDir, path)
-		if err != nil {
-			flog.Fatalf("getting relative path: %v", err)
-		}
-		child := cliCommandRoute(cmd)
-		child.Path = relPath
-		cmdLine.Children = append(cmdLine.Children, child)
-	}
-	// Sort children by title because wroteMap iteration is non-deterministic.
-	slices.SortFunc(cmdLine.Children, func(a, b docgenenv.Route) int {
-		return cmp.Compare(a.Title, b.Title)
-	})
-
-	manifestByt, err := json.MarshalIndent(man, "", "  ")
-	if err != nil {
-		flog.Fatalf("marshaling manifest: %v", err)
-	}
-
-	err = atomicwrite.File(manifestPath, manifestByt)
-	if err != nil {
-		flog.Fatalf("writing manifest: %v", err)
-	}
 }
diff --git a/scripts/clidocgen/route_test.go b/scripts/clidocgen/route_test.go
index 3b8dad0901..9b6f3ad5d9 100644
--- a/scripts/clidocgen/route_test.go
+++ b/scripts/clidocgen/route_test.go
@@ -9,21 +9,95 @@ import (
 	"github.com/coder/serpent"
 )
 
+// commandTree is a small command tree shaped like the real one: "coder" with
+// a leaf ("ping"), a nested group ("users" > "roles" > "list"), and a hidden
+// command that must not get a page or nav entry.
+type commandTree struct {
+	root, ping, users, roles, list *serpent.Command
+}
+
+func newCommandTree() commandTree {
+	tr := commandTree{
+		root:  &serpent.Command{Use: "coder"},
+		ping:  &serpent.Command{Use: "ping <workspace>", Short: "Ping a workspace"},
+		users: &serpent.Command{Use: "users", Short: "Manage users"},
+		roles: &serpent.Command{Use: "roles", Short: "Manage user roles"},
+		list:  &serpent.Command{Use: "list", Short: "List user roles"},
+	}
+	tr.roles.AddSubcommands(tr.list)
+	tr.users.AddSubcommands(tr.roles, &serpent.Command{Use: "secret", Hidden: true})
+	tr.root.AddSubcommands(tr.users, tr.ping)
+	return tr
+}
+
 // TestCLICommandRoute pins the per-command metadata mapping the CLI generator
-// mirrors into page front matter: title from the command's full name and
-// description from its Short, with no curated fields invented. Path, IconPath,
-// and State stay zero here (Path is layered on by the manifest rebuild;
-// IconPath/State are index/manifest-authored only), so the shared emitter
-// cannot silently gain a CLI-only value.
+// mirrors into page front matter: the title is the full invocation as inline
+// code and the description is the command's Short, with no curated fields
+// invented. Path, IconPath, and State stay zero so the shared emitter cannot
+// silently gain a CLI-only value.
 func TestCLICommandRoute(t *testing.T) {
 	t.Parallel()
 
-	got := cliCommandRoute(&serpent.Command{Use: "ping", Short: "Ping a workspace"})
-	require.Equal(t, "ping", got.Title)
-	require.Equal(t, "Ping a workspace", got.Description)
+	got := cliCommandRoute(newCommandTree().list)
+	require.Equal(t, "`coder users roles list`", got.Title)
+	require.Equal(t, "List user roles", got.Description)
 	require.Empty(t, got.Path)
 	require.Empty(t, got.IconPath)
 	require.Nil(t, got.State)
+	require.Contains(t, docgenenv.FrontMatter(got), "title: \"`coder users roles list`\"\n")
+}
+
+// TestFmtDocFilename pins the page layout: pages nest by command path, and a
+// command with visible subcommands is the index.md of its own directory.
+func TestFmtDocFilename(t *testing.T) {
+	t.Parallel()
+
+	tr := newCommandTree()
+	require.Equal(t, "index.md", fmtDocFilename(tr.root))
+	require.Equal(t, "ping.md", fmtDocFilename(tr.ping))
+	require.Equal(t, "users/index.md", fmtDocFilename(tr.users))
+	require.Equal(t, "users/roles/index.md", fmtDocFilename(tr.roles))
+	require.Equal(t, "users/roles/list.md", fmtDocFilename(tr.list))
+}
+
+// TestSubcommandLink pins the Subcommands table links, which are relative to
+// the parent page's directory.
+func TestSubcommandLink(t *testing.T) {
+	t.Parallel()
+
+	tr := newCommandTree()
+	require.Equal(t, "./ping.md", subcommandLink(tr.ping))
+	require.Equal(t, "./users/index.md", subcommandLink(tr.users))
+	require.Equal(t, "./roles/index.md", subcommandLink(tr.roles))
+	require.Equal(t, "./list.md", subcommandLink(tr.list))
+}
+
+// TestCLIManifestChildren pins the nested nav: entries are sorted by name,
+// titled with only their own verb as inline code, point at the nested page
+// path, and skip hidden commands.
+func TestCLIManifestChildren(t *testing.T) {
+	t.Parallel()
+
+	got := cliManifestChildren(newCommandTree().root)
+	want := []docgenenv.Route{
+		{Title: "`ping`", Description: "Ping a workspace", Path: "reference/cli/ping.md"},
+		{
+			Title:       "`users`",
+			Description: "Manage users",
+			Path:        "reference/cli/users/index.md",
+			Children: []docgenenv.Route{{
+				Title:       "`roles`",
+				Description: "Manage user roles",
+				Path:        "reference/cli/users/roles/index.md",
+				Children: []docgenenv.Route{{
+					Title:       "`list`",
+					Description: "List user roles",
+					Path:        "reference/cli/users/roles/list.md",
+				}},
+			}},
+		},
+	}
+	require.Equal(t, want, got)
 }
 
 // TestCLIIndexRouteMirrorsManifest pins the CLI index page's route: it copies
diff --git a/scripts/configdocgen/main.go b/scripts/configdocgen/main.go
index 6e9149cd82..accf7d68bb 100644
--- a/scripts/configdocgen/main.go
+++ b/scripts/configdocgen/main.go
@@ -44,7 +44,7 @@ only the methods that apply to it.
 - A key in a YAML configuration file passed with ` + "`--config`" + `.
 
 For a full description of each option's accepted values and behavior, follow the
-flag link into the [` + "`coder server`" + ` CLI reference](../../reference/cli/server.md).
+flag link into the [` + "`coder server`" + ` CLI reference](../../reference/cli/server/index.md).
 
 Deprecated options are listed at the end of each section.
 
@@ -338,7 +338,7 @@ func renderOption(b *strings.Builder, opt option, level int) {
 		_, _ = fmt.Fprintf(b, "- Environment variable: `%s`\n", opt.env)
 	}
 	if opt.flagName != "" {
-		_, _ = fmt.Fprintf(b, "- CLI flag: [`%s`](../../reference/cli/server.md#%s)\n", opt.flagName, opt.flagAnchor)
+		_, _ = fmt.Fprintf(b, "- CLI flag: [`%s`](../../reference/cli/server/index.md#%s)\n", opt.flagName, opt.flagAnchor)
 	}
 	if opt.yaml != "" {
 		_, _ = fmt.Fprintf(b, "- YAML key: `%s`\n", opt.yaml)
diff --git a/scripts/configdocgen/main_test.go b/scripts/configdocgen/main_test.go
index 571dde2193..49a3bc6138 100644
--- a/scripts/configdocgen/main_test.go
+++ b/scripts/configdocgen/main_test.go
@@ -235,12 +235,12 @@ func TestRenderPipeline(t *testing.T) {
 		"## General",
 		"### Access URL",
 		"- Environment variable: `CODER_ACCESS_URL`",
-		"- CLI flag: [`--access-url`](../../reference/cli/server.md#--access-url)",
+		"- CLI flag: [`--access-url`](../../reference/cli/server/index.md#--access-url)",
 		"- Default value: `https://example.com`",
 		"## Email",
 		"### Smarthost",
 		// Flag shorthand is folded into the anchor to match the CLI reference.
-		"- CLI flag: [`--email-smarthost`](../../reference/cli/server.md#-s---email-smarthost)",
+		"- CLI flag: [`--email-smarthost`](../../reference/cli/server/index.md#-s---email-smarthost)",
 		// YAML key is the dotted group path.
 		"- YAML key: `email.from`",
 		// Deprecated marker is prepended for the UseInstead path.