diff --git a/site/src/components/Resources/AgentOutdatedTooltip.tsx b/site/src/components/Resources/AgentOutdatedTooltip.tsx
index 6bbe9061d1..8901b22385 100644
--- a/site/src/components/Resources/AgentOutdatedTooltip.tsx
+++ b/site/src/components/Resources/AgentOutdatedTooltip.tsx
@@ -2,25 +2,28 @@ import { type ComponentProps, type FC } from "react";
 import { useTheme } from "@emotion/react";
 import RefreshIcon from "@mui/icons-material/RefreshOutlined";
 import {
-  HelpTooltipText,
   HelpPopover,
-  HelpTooltipTitle,
   HelpTooltipAction,
-  HelpTooltipLinksGroup,
   HelpTooltipContext,
+  HelpTooltipLinksGroup,
+  HelpTooltipText,
+  HelpTooltipTitle,
 } from "components/HelpTooltip/HelpTooltip";
 import type { WorkspaceAgent } from "api/typesGenerated";
 import { Stack } from "components/Stack/Stack";
+import { agentVersionStatus } from "../../utils/workspace";
 
 type AgentOutdatedTooltipProps = ComponentProps<typeof HelpPopover> & {
   agent: WorkspaceAgent;
   serverVersion: string;
+  status: agentVersionStatus;
   onUpdate: () => void;
 };
 
 export const AgentOutdatedTooltip: FC<AgentOutdatedTooltipProps> = ({
   agent,
   serverVersion,
+  status,
   onUpdate,
   onOpen,
   id,
@@ -33,6 +36,18 @@ export const AgentOutdatedTooltip: FC<AgentOutdatedTooltipProps> = ({
     fontWeight: 600,
     color: theme.palette.text.primary,
   };
+  const title =
+    status === agentVersionStatus.Outdated
+      ? "Agent Outdated"
+      : "Agent Deprecated";
+  const opener =
+    status === agentVersionStatus.Outdated
+      ? "This agent is an older version than the Coder server."
+      : "This agent is using a deprecated version of the API.";
+  const text =
+    opener +
+    " This can happen after you update Coder with running workspaces. " +
+    "To fix this, you can stop and start the workspace.";
 
   return (
     <HelpPopover
@@ -45,12 +60,8 @@ export const AgentOutdatedTooltip: FC<AgentOutdatedTooltipProps> = ({
       <HelpTooltipContext.Provider value={{ open, onClose }}>
         <Stack spacing={1}>
           <div>
-            <HelpTooltipTitle>Agent Outdated</HelpTooltipTitle>
-            <HelpTooltipText>
-              This agent is an older version than the Coder server. This can
-              happen after you update Coder with running workspaces. To fix
-              this, you can stop and start the workspace.
-            </HelpTooltipText>
+            <HelpTooltipTitle>{title}</HelpTooltipTitle>
+            <HelpTooltipText>{text}</HelpTooltipText>
           </div>
 
           <Stack spacing={0.5}>
diff --git a/site/src/components/Resources/AgentRow.stories.tsx b/site/src/components/Resources/AgentRow.stories.tsx
index 1c73aa7f78..f4a08edbed 100644
--- a/site/src/components/Resources/AgentRow.stories.tsx
+++ b/site/src/components/Resources/AgentRow.stories.tsx
@@ -14,9 +14,10 @@ import {
   MockWorkspaceAgentStarting,
   MockWorkspaceAgentStartTimeout,
   MockWorkspaceAgentTimeout,
+  MockWorkspaceAgentLogSource,
+  MockWorkspaceAgentDeprecated,
   MockWorkspaceApp,
   MockProxyLatencies,
-  MockWorkspaceAgentLogSource,
 } from "testHelpers/entities";
 import { AgentRow, LineWithID } from "./AgentRow";
 import { ProxyContext, getPreferredProxy } from "contexts/ProxyContext";
@@ -287,5 +288,15 @@ export const Outdated: Story = {
     agent: MockWorkspaceAgentOutdated,
     workspace: MockWorkspace,
     serverVersion: "v99.999.9999+c1cdf14",
+    serverAPIVersion: "1.0",
+  },
+};
+
+export const Deprecated: Story = {
+  args: {
+    agent: MockWorkspaceAgentDeprecated,
+    workspace: MockWorkspace,
+    serverVersion: "v99.999.9999+c1cdf14",
+    serverAPIVersion: "2.0",
   },
 };
diff --git a/site/src/components/Resources/AgentRow.tsx b/site/src/components/Resources/AgentRow.tsx
index 4bff9c76db..a908f1caac 100644
--- a/site/src/components/Resources/AgentRow.tsx
+++ b/site/src/components/Resources/AgentRow.tsx
@@ -55,6 +55,7 @@ export interface AgentRowProps {
   hideSSHButton?: boolean;
   hideVSCodeDesktopButton?: boolean;
   serverVersion: string;
+  serverAPIVersion: string;
   onUpdateAgent: () => void;
   storybookLogs?: LineWithID[];
   storybookAgentMetadata?: WorkspaceAgentMetadata[];
@@ -68,6 +69,7 @@ export const AgentRow: FC<AgentRowProps> = ({
   hideSSHButton,
   hideVSCodeDesktopButton,
   serverVersion,
+  serverAPIVersion,
   onUpdateAgent,
   storybookAgentMetadata,
   sshPrefix,
@@ -179,6 +181,7 @@ export const AgentRow: FC<AgentRowProps> = ({
                   <AgentVersion
                     agent={agent}
                     serverVersion={serverVersion}
+                    serverAPIVersion={serverAPIVersion}
                     onUpdate={onUpdateAgent}
                   />
                   <AgentLatency agent={agent} />
diff --git a/site/src/components/Resources/AgentVersion.tsx b/site/src/components/Resources/AgentVersion.tsx
index 98b358a92a..e353802145 100644
--- a/site/src/components/Resources/AgentVersion.tsx
+++ b/site/src/components/Resources/AgentVersion.tsx
@@ -1,19 +1,25 @@
 import { type FC, useRef, useState } from "react";
 import type { WorkspaceAgent } from "api/typesGenerated";
-import { getDisplayVersionStatus } from "utils/workspace";
+import { agentVersionStatus, getDisplayVersionStatus } from "utils/workspace";
 import { AgentOutdatedTooltip } from "./AgentOutdatedTooltip";
 
 export const AgentVersion: FC<{
   agent: WorkspaceAgent;
   serverVersion: string;
+  serverAPIVersion: string;
   onUpdate: () => void;
-}> = ({ agent, serverVersion, onUpdate }) => {
+}> = ({ agent, serverVersion, serverAPIVersion, onUpdate }) => {
   const anchorRef = useRef<HTMLButtonElement>(null);
   const [isOpen, setIsOpen] = useState(false);
   const id = isOpen ? "version-outdated-popover" : undefined;
-  const { outdated } = getDisplayVersionStatus(agent.version, serverVersion);
+  const { status } = getDisplayVersionStatus(
+    agent.version,
+    serverVersion,
+    agent.api_version,
+    serverAPIVersion,
+  );
 
-  if (!outdated) {
+  if (status === agentVersionStatus.Updated) {
     return <span>Updated</span>;
   }
 
@@ -27,7 +33,7 @@ export const AgentVersion: FC<{
         onMouseLeave={() => setIsOpen(false)}
         css={{ cursor: "pointer" }}
       >
-        Outdated
+        {status === agentVersionStatus.Outdated ? "Outdated" : "Deprecated"}
       </span>
       <AgentOutdatedTooltip
         id={id}
@@ -37,6 +43,7 @@ export const AgentVersion: FC<{
         onClose={() => setIsOpen(false)}
         agent={agent}
         serverVersion={serverVersion}
+        status={status}
         onUpdate={onUpdate}
       />
     </>
diff --git a/site/src/components/Resources/ResourceCard.stories.tsx b/site/src/components/Resources/ResourceCard.stories.tsx
index 2759ab4bd5..576ef68db7 100644
--- a/site/src/components/Resources/ResourceCard.stories.tsx
+++ b/site/src/components/Resources/ResourceCard.stories.tsx
@@ -99,6 +99,7 @@ function getAgentRow(agent: WorkspaceAgent): JSX.Element {
         agent={agent}
         workspace={MockWorkspace}
         serverVersion=""
+        serverAPIVersion=""
         onUpdateAgent={action("updateAgent")}
       />
     </ProxyContext.Provider>
diff --git a/site/src/components/Resources/Resources.stories.tsx b/site/src/components/Resources/Resources.stories.tsx
index 32cde805cf..0a7693f5b4 100644
--- a/site/src/components/Resources/Resources.stories.tsx
+++ b/site/src/components/Resources/Resources.stories.tsx
@@ -195,6 +195,7 @@ function getAgentRow(agent: WorkspaceAgent): JSX.Element {
         agent={agent}
         workspace={MockWorkspace}
         serverVersion=""
+        serverAPIVersion=""
         onUpdateAgent={action("updateAgent")}
       />
     </ProxyContext.Provider>
diff --git a/site/src/pages/WorkspacePage/Workspace.tsx b/site/src/pages/WorkspacePage/Workspace.tsx
index 0aa7a3d742..08b278bec5 100644
--- a/site/src/pages/WorkspacePage/Workspace.tsx
+++ b/site/src/pages/WorkspacePage/Workspace.tsx
@@ -357,6 +357,7 @@ export const Workspace: FC<React.PropsWithChildren<WorkspaceProps>> = ({
                   hideSSHButton={hideSSHButton}
                   hideVSCodeDesktopButton={hideVSCodeDesktopButton}
                   serverVersion={buildInfo?.version || ""}
+                  serverAPIVersion={buildInfo?.agent_api_version || ""}
                   onUpdateAgent={handleUpdate} // On updating the workspace the agent version is also updated
                 />
               )}
diff --git a/site/src/testHelpers/entities.ts b/site/src/testHelpers/entities.ts
index bab25c74e7..139df91c2e 100644
--- a/site/src/testHelpers/entities.ts
+++ b/site/src/testHelpers/entities.ts
@@ -194,7 +194,7 @@ export const MockProxyLatencies: Record<string, ProxyLatencyReport> = {
 };
 
 export const MockBuildInfo: TypesGen.BuildInfoResponse = {
-  agent_api_version: "2.1",
+  agent_api_version: "1.0",
   external_url: "file:///mock-url",
   version: "v99.999.9999+c9cdf14",
   dashboard_url: "https:///mock-url",
@@ -645,6 +645,31 @@ export const MockWorkspaceAgentOutdated: TypesGen.WorkspaceAgent = {
   lifecycle_state: "ready",
 };
 
+export const MockWorkspaceAgentDeprecated: TypesGen.WorkspaceAgent = {
+  ...MockWorkspaceAgent,
+  id: "test-workspace-agent-3",
+  name: "an-outdated-workspace-agent",
+  version: "v99.999.9998+abcdef",
+  api_version: "1.99",
+  operating_system: "Windows",
+  latency: {
+    ...MockWorkspaceAgent.latency,
+    Chicago: {
+      preferred: false,
+      latency_ms: 95.11,
+    },
+    "San Francisco": {
+      preferred: false,
+      latency_ms: 111.55,
+    },
+    Paris: {
+      preferred: false,
+      latency_ms: 221.66,
+    },
+  },
+  lifecycle_state: "ready",
+};
+
 export const MockWorkspaceAgentConnecting: TypesGen.WorkspaceAgent = {
   ...MockWorkspaceAgent,
   id: "test-workspace-agent-connecting",
diff --git a/site/src/utils/workspace.test.ts b/site/src/utils/workspace.test.ts
index f7385eb850..3d267acf5f 100644
--- a/site/src/utils/workspace.test.ts
+++ b/site/src/utils/workspace.test.ts
@@ -2,6 +2,7 @@ import dayjs from "dayjs";
 import * as TypesGen from "api/typesGenerated";
 import * as Mocks from "testHelpers/entities";
 import {
+  agentVersionStatus,
   defaultWorkspaceExtension,
   getDisplayVersionStatus,
   getDisplayWorkspaceBuildInitiatedBy,
@@ -101,23 +102,40 @@ describe("util > workspace", () => {
   });
 
   describe("getDisplayVersionStatus", () => {
-    it.each<[string, string, string, boolean]>([
-      ["", "", "Unknown", false],
-      ["", "v1.2.3", "Unknown", false],
-      ["v1.2.3", "", "v1.2.3", false],
-      ["v1.2.3", "v1.2.3", "v1.2.3", false],
-      ["v1.2.3", "v1.2.4", "v1.2.3", true],
-      ["v1.2.4", "v1.2.3", "v1.2.4", false],
-      ["foo", "bar", "foo", false],
+    it.each<[string, string, string, string, string, agentVersionStatus]>([
+      ["", "", "", "", "Unknown", agentVersionStatus.Updated],
+      ["", "v1.2.3", "", "", "Unknown", agentVersionStatus.Updated],
+      ["v1.2.3", "", "", "", "v1.2.3", agentVersionStatus.Updated],
+      ["v1.2.3", "v1.2.3", "", "", "v1.2.3", agentVersionStatus.Updated],
+      ["v1.2.3", "v1.2.4", "", "", "v1.2.3", agentVersionStatus.Outdated],
+      ["v1.2.4", "v1.2.3", "", "", "v1.2.4", agentVersionStatus.Updated],
+      ["foo", "bar", "", "", "foo", agentVersionStatus.Updated],
+      [
+        "v1.2.3",
+        "v1.2.4",
+        "1.8",
+        "2.1",
+        "v1.2.3",
+        agentVersionStatus.Deprecated,
+      ],
     ])(
-      `getDisplayVersionStatus(theme, %p, %p) returns (%p, %p)`,
-      (agentVersion, serverVersion, expectedVersion, expectedOutdated) => {
-        const { displayVersion, outdated } = getDisplayVersionStatus(
+      `getDisplayVersionStatus(theme, %p, %p, %p, %p) returns (%p, %p)`,
+      (
+        agentVersion,
+        serverVersion,
+        agentAPIVersion,
+        serverAPIVersion,
+        expectedVersion,
+        expectedStatus,
+      ) => {
+        const { displayVersion, status } = getDisplayVersionStatus(
           agentVersion,
           serverVersion,
+          agentAPIVersion,
+          serverAPIVersion,
         );
         expect(displayVersion).toEqual(expectedVersion);
-        expect(expectedOutdated).toEqual(outdated);
+        expect(status).toEqual(expectedStatus);
       },
     );
   });
diff --git a/site/src/utils/workspace.tsx b/site/src/utils/workspace.tsx
index db68597e1a..ac0eb1407a 100644
--- a/site/src/utils/workspace.tsx
+++ b/site/src/utils/workspace.tsx
@@ -108,26 +108,38 @@ export const displayWorkspaceBuildDuration = (
   return duration ? `${duration} seconds` : inProgressLabel;
 };
 
+export const enum agentVersionStatus {
+  Updated = 1,
+  Outdated = 2,
+  Deprecated = 3,
+}
+
 export const getDisplayVersionStatus = (
   agentVersion: string,
   serverVersion: string,
-): { displayVersion: string; outdated: boolean } => {
-  if (!semver.valid(serverVersion) || !semver.valid(agentVersion)) {
-    return {
-      displayVersion: agentVersion || DisplayAgentVersionLanguage.unknown,
-      outdated: false,
-    };
-  } else if (semver.lt(agentVersion, serverVersion)) {
-    return {
-      displayVersion: agentVersion,
-      outdated: true,
-    };
-  } else {
-    return {
-      displayVersion: agentVersion,
-      outdated: false,
-    };
+  agentAPIVersion: string,
+  serverAPIVersion: string,
+): { displayVersion: string; status: agentVersionStatus } => {
+  // APIVersions only have major.minor so coerce them to major.minor.0, so we can use semver.major()
+  const a = semver.coerce(agentAPIVersion);
+  const s = semver.coerce(serverAPIVersion);
+  let status = agentVersionStatus.Updated;
+  if (
+    semver.valid(agentVersion) &&
+    semver.valid(serverVersion) &&
+    semver.lt(agentVersion, serverVersion)
+  ) {
+    status = agentVersionStatus.Outdated;
   }
+  // deprecated overrides and implies Outdated
+  if (a !== null && s !== null && semver.major(a) < semver.major(s)) {
+    status = agentVersionStatus.Deprecated;
+  }
+  const displayVersion = agentVersion || DisplayAgentVersionLanguage.unknown;
+  return {
+    displayVersion: displayVersion,
+    status: status,
+  };
 };
 
 export const isWorkspaceOn = (workspace: TypesGen.Workspace): boolean => {