diff --git a/docs/img/headless/approval.png b/docs/img/headless/approval.png
new file mode 100644
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diff --git a/docs/img/headless/confirmation.png b/docs/img/headless/confirmation.png
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diff --git a/docs/pages/access-controls/guides/headless.mdx b/docs/pages/access-controls/guides/headless.mdx
index 3fd5b304403..fd021da4378 100644
--- a/docs/pages/access-controls/guides/headless.mdx
+++ b/docs/pages/access-controls/guides/headless.mdx
@@ -35,6 +35,7 @@ For example:
 - Machines for Headless WebAuthn activities have [Linux](../../installation.mdx#linux), [macOS](../../installation.mdx#macos) or [Windows](../../installation.mdx#windows-tsh-client-only) `tsh` binary v12.2+ installed.
 - Machines used to approve Headless WebAuthn requests have a Web browser with [WebAuthn support](
   https://developers.yubico.com/WebAuthn/WebAuthn_Browser_Support/) or `tsh` binary v12.2+ installed.
+- Optional: Teleport Connect v13.3.1+ for [seamless Headless WebAuthn approval](#optional-teleport-connect).
 
 ## Step 1/3. Configuration
 
@@ -178,6 +179,25 @@ alice@server01 $
   your local terminal.
 </Notice>
 
+## Optional: Teleport Connect
+
+Teleport Connect v13.3.1+ can also be used to approve Headless WebAuthn logins.
+Teleport Connect will automatically detect the Headless WebAuthn login attempt
+and allow you to approve or cancel the request.
+
+<Figure width="700">
+![Headless Confirmation](../../../img/headless/confirmation.png)
+</Figure>
+
+You will be prompted to tap your MFA key to complete the approval process.
+
+<Figure width="700">
+![Headless WebAuthn Approval](../../../img/headless/approval.png)
+</Figure>
+
+<Notice type="note">
+  This also requires a v13.3.1+ Teleport Auth Service.
+</Notice>
 
 ## Troubleshooting
 
diff --git a/docs/pages/connect-your-client/teleport-connect.mdx b/docs/pages/connect-your-client/teleport-connect.mdx
index cf01e40e3b6..a743585ac2e 100644
--- a/docs/pages/connect-your-client/teleport-connect.mdx
+++ b/docs/pages/connect-your-client/teleport-connect.mdx
@@ -212,6 +212,7 @@ Below is the list of the supported config properties.
 | `keymap.openClusters`         | `Command+E` on macOS<br/>`Ctrl+E` on Windows/Linux                                                                   | Shortcut to open the cluster selector.                                 |
 | `keymap.openProfiles`         | `Command+I` on macOS<br/>`Ctrl+I` on Windows/Linux                                                                   | Shortcut to open the profile selector.                                 |
 | `keymap.openSearchBar`        | `Command+K` on macOS<br/>`Ctrl+K` on Windows/Linux                                                                   | Shortcut to open the search bar.                                       |
+| `headless.skipConfirm` | false | Skips the confirmation prompt for Headless WebAuthn approval and instead prompts for WebAuthn immediately. |
 
 <Admonition
   type="note"