diff --git a/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx b/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx
index 6de6f2c40d..5f6a415220 100644
--- a/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx
+++ b/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx
@@ -13,10 +13,11 @@ import {
 	HelpTooltipLinksGroup,
 	HelpTooltipText,
 	HelpTooltipTitle,
+	HelpTooltipTrigger,
 } from "components/HelpTooltip/HelpTooltip";
 import { InfoIcon, RotateCcwIcon } from "lucide-react";
 import { linkToTemplate, useLinks } from "modules/navigation";
-import { type FC, useState } from "react";
+import { type FC, type ReactNode, useState } from "react";
 import { useQuery } from "react-query";
 import {
 	useWorkspaceUpdate,
@@ -25,20 +26,31 @@ import {
 
 interface WorkspaceOutdatedTooltipProps {
 	workspace: Workspace;
+	children?: ReactNode;
 }
 
-export const WorkspaceOutdatedTooltip: FC<WorkspaceOutdatedTooltipProps> = (
-	props,
-) => {
+export const WorkspaceOutdatedTooltip: FC<WorkspaceOutdatedTooltipProps> = ({
+	workspace,
+	children,
+}) => {
 	const [isOpen, setIsOpen] = useState(false);
 
 	return (
 		<HelpTooltip open={isOpen} onOpenChange={setIsOpen}>
-			<HelpTooltipIconTrigger size="small" hoverEffect={false}>
-				<InfoIcon css={styles.icon} />
-				<span className="sr-only">Outdated info</span>
-			</HelpTooltipIconTrigger>
-			<WorkspaceOutdatedTooltipContent isOpen={isOpen} {...props} />
+			{children ? (
+				<HelpTooltipTrigger asChild>
+					<span className="flex items-center gap-1.5 cursor-help">
+						<InfoIcon css={styles.icon} size={14} />
+						<span>{children}</span>
+					</span>
+				</HelpTooltipTrigger>
+			) : (
+				<HelpTooltipIconTrigger size="small" hoverEffect={false}>
+					<InfoIcon css={styles.icon} />
+					<span className="sr-only">Outdated info</span>
+				</HelpTooltipIconTrigger>
+			)}
+			<WorkspaceOutdatedTooltipContent isOpen={isOpen} workspace={workspace} />
 		</HelpTooltip>
 	);
 };
diff --git a/site/src/pages/TaskPage/TaskPage.stories.tsx b/site/src/pages/TaskPage/TaskPage.stories.tsx
index cfe4c90a65..581b331b7b 100644
--- a/site/src/pages/TaskPage/TaskPage.stories.tsx
+++ b/site/src/pages/TaskPage/TaskPage.stories.tsx
@@ -19,6 +19,7 @@ import {
 } from "testHelpers/entities";
 import {
 	withAuthProvider,
+	withDashboardProvider,
 	withGlobalSnackbar,
 	withProxyProvider,
 	withWebSocket,
@@ -65,7 +66,7 @@ const MockVSCodeApp: WorkspaceApp = {
 const meta: Meta<typeof TaskPage> = {
 	title: "pages/TaskPage",
 	component: TaskPage,
-	decorators: [withProxyProvider(), withAuthProvider],
+	decorators: [withProxyProvider(), withAuthProvider, withDashboardProvider],
 	beforeEach: () => {
 		spyOn(API, "getTasks").mockResolvedValue(MockTasks);
 	},
@@ -402,6 +403,50 @@ export const MainAppHealthy: Story = mainAppHealthStory("healthy");
 export const MainAppInitializing: Story = mainAppHealthStory("initializing");
 export const MainAppUnhealthy: Story = mainAppHealthStory("unhealthy");
 
+export const OutdatedWorkspace: Story = {
+	// Given: an 'outdated' workspace (that is, the latest build does not use template's active version)
+	parameters: {
+		queries: [
+			{
+				key: ["tasks", { owner: MockTask.owner_name }],
+				data: [MockTask],
+			},
+			{
+				key: ["tasks", MockTask.owner_name, MockTask.id],
+				data: MockTask,
+			},
+			{
+				key: [
+					"workspace",
+					MockTask.owner_name,
+					MockTask.workspace_name,
+					"settings",
+				],
+				data: {
+					...MockStoppedWorkspace,
+					outdated: true,
+				},
+			},
+			{
+				key: [
+					"workspaceBuilds",
+					MockStoppedWorkspace.latest_build.id,
+					"parameters",
+				],
+				data: [],
+			},
+		],
+	},
+	// Then: a tooltip should be displayed prompting the user to update the workspace.
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const outdatedTooltip = await canvas.findByTestId(
+			"workspace-outdated-tooltip",
+		);
+		expect(outdatedTooltip).toBeVisible();
+	},
+};
+
 export const Active: Story = {
 	decorators: [withProxyProvider()],
 	beforeEach: () => {
diff --git a/site/src/pages/TaskPage/TaskPage.tsx b/site/src/pages/TaskPage/TaskPage.tsx
index 56da12468c..0808fe851d 100644
--- a/site/src/pages/TaskPage/TaskPage.tsx
+++ b/site/src/pages/TaskPage/TaskPage.tsx
@@ -26,6 +26,7 @@ import { getAllAppsWithAgent } from "modules/tasks/apps";
 import { TasksSidebar } from "modules/tasks/TasksSidebar/TasksSidebar";
 import { WorkspaceErrorDialog } from "modules/workspaces/ErrorDialog/WorkspaceErrorDialog";
 import { WorkspaceBuildLogs } from "modules/workspaces/WorkspaceBuildLogs/WorkspaceBuildLogs";
+import { WorkspaceOutdatedTooltip } from "modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip";
 import {
 	type FC,
 	type PropsWithChildren,
@@ -275,9 +276,20 @@ const WorkspaceNotRunning: FC<WorkspaceNotRunningProps> = ({
 					<span className="text-content-secondary text-sm">
 						Apps and previous statuses are not available
 					</span>
+					{workspace.outdated && (
+						<div
+							data-testid="workspace-outdated-tooltip"
+							className="flex items-center gap-1.5 mt-1 text-content-secondary text-sm"
+						>
+							<WorkspaceOutdatedTooltip workspace={workspace}>
+								You can update your task workspace to a newer version
+							</WorkspaceOutdatedTooltip>
+						</div>
+					)}
 					<div className="flex flex-row mt-4 gap-4">
 						<Button
 							size="sm"
+							data-testid="task-start-workspace"
 							disabled={isWaitingForStart}
 							onClick={() => {
 								mutateStartWorkspace.mutate({