diff --git a/site/src/pages/TaskPage/TaskPage.stories.tsx b/site/src/pages/TaskPage/TaskPage.stories.tsx
index b247a2a16b377..27f0b60e3a16f 100644
--- a/site/src/pages/TaskPage/TaskPage.stories.tsx
+++ b/site/src/pages/TaskPage/TaskPage.stories.tsx
@@ -7,6 +7,7 @@ import {
 	MockTasks,
 	MockUserOwner,
 	MockWorkspace,
+	MockWorkspaceAgent,
 	MockWorkspaceAgentLogSource,
 	MockWorkspaceAgentReady,
 	MockWorkspaceAgentStarting,
@@ -218,6 +219,117 @@ export const WaitingStartupScripts: Story = {
 	},
 };
 
+export const StartupScriptError: Story = {
+	decorators: [withWebSocket],
+	parameters: {
+		queries: [
+			{
+				key: ["tasks", MockTask.owner_name, MockTask.id],
+				data: {
+					...MockTask,
+					workspace_agent_lifecycle: "start_error",
+				},
+			},
+			{
+				key: [
+					"workspace",
+					MockTask.owner_name,
+					MockTask.workspace_name,
+					"settings",
+				],
+				data: {
+					...MockWorkspace,
+					latest_build: {
+						...MockWorkspace.latest_build,
+						has_ai_task: true,
+						resources: [
+							{
+								...MockWorkspaceResource,
+								agents: [MockWorkspaceAgent],
+							},
+						],
+					},
+				},
+			},
+		],
+		webSocket: [
+			{
+				event: "message",
+				data: JSON.stringify(
+					[
+						"Cloning Git repository...",
+						"Starting application...",
+						"\x1b[91mError: Failed to connect to database",
+						"\x1b[91mStartup script exited with code 1",
+					].map((line, index) => ({
+						id: index,
+						level: index >= 2 ? "error" : "info",
+						output: line,
+						source_id: MockWorkspaceAgentLogSource.id,
+						created_at: new Date("2024-01-01T12:00:00Z").toISOString(),
+					})),
+				),
+			},
+		],
+	},
+};
+
+export const StartupScriptTimeout: Story = {
+	decorators: [withWebSocket],
+	parameters: {
+		queries: [
+			{
+				key: ["tasks", MockTask.owner_name, MockTask.id],
+				data: {
+					...MockTask,
+					workspace_agent_lifecycle: "start_timeout",
+				},
+			},
+			{
+				key: [
+					"workspace",
+					MockTask.owner_name,
+					MockTask.workspace_name,
+					"settings",
+				],
+				data: {
+					...MockWorkspace,
+					latest_build: {
+						...MockWorkspace.latest_build,
+						has_ai_task: true,
+						resources: [
+							{
+								...MockWorkspaceResource,
+								agents: [MockWorkspaceAgent],
+							},
+						],
+					},
+				},
+			},
+		],
+		webSocket: [
+			{
+				event: "message",
+				data: JSON.stringify(
+					[
+						"Cloning Git repository...",
+						"Starting application...",
+						"Waiting for dependencies...",
+						"Still waiting...",
+						"\x1b[93mWarning: Startup script exceeded timeout limit",
+					].map((line, index) => ({
+						id: index,
+						level: index === 4 ? "warn" : "info",
+						output: line,
+						source_id: MockWorkspaceAgentLogSource.id,
+						created_at: new Date("2024-01-01T12:00:00Z").toISOString(),
+					})),
+				),
+			},
+		],
+	},
+};
+
 export const SidebarAppNotFound: Story = {
 	beforeEach: () => {
 		const [task, workspace] = mockTaskWithWorkspace(
diff --git a/site/src/pages/TaskPage/TaskStartupWarningButton.stories.tsx b/site/src/pages/TaskPage/TaskStartupWarningButton.stories.tsx
new file mode 100644
index 0000000000000..482fa396016d7
--- /dev/null
+++ b/site/src/pages/TaskPage/TaskStartupWarningButton.stories.tsx
@@ -0,0 +1,37 @@
+import type { Meta, StoryObj } from "@storybook/react-vite";
+import { TaskStartupWarningButton } from "./TaskStartupWarningButton";
+
+const meta: Meta<typeof TaskStartupWarningButton> = {
+	title: "pages/TaskPage/TaskStartupWarningButton",
+	component: TaskStartupWarningButton,
+	parameters: {
+		layout: "padded",
+	},
+};
+
+export default meta;
+type Story = StoryObj<typeof TaskStartupWarningButton>;
+
+export const StartError: Story = {
+	args: {
+		lifecycleState: "start_error",
+	},
+};
+
+export const StartTimeout: Story = {
+	args: {
+		lifecycleState: "start_timeout",
+	},
+};
+
+export const NoWarning: Story = {
+	args: {
+		lifecycleState: "ready",
+	},
+};
+
+export const NullLifecycle: Story = {
+	args: {
+		lifecycleState: null,
+	},
+};
diff --git a/site/src/pages/TaskPage/TaskStartupWarningButton.tsx b/site/src/pages/TaskPage/TaskStartupWarningButton.tsx
new file mode 100644
index 0000000000000..fab1b1a9b32e6
--- /dev/null
+++ b/site/src/pages/TaskPage/TaskStartupWarningButton.tsx
@@ -0,0 +1,109 @@
+import type { WorkspaceAgentLifecycle } from "api/typesGenerated";
+import { Button } from "components/Button/Button";
+import { Link } from "components/Link/Link";
+import {
+	Tooltip,
+	TooltipContent,
+	TooltipProvider,
+	TooltipTrigger,
+} from "components/Tooltip/Tooltip";
+import { TriangleAlertIcon } from "lucide-react";
+import type { FC } from "react";
+import { docs } from "utils/docs";
+
+type TaskStartupWarningButtonProps = {
+	lifecycleState?: WorkspaceAgentLifecycle | null;
+};
+
+export const TaskStartupWarningButton: FC<TaskStartupWarningButtonProps> = ({
+	lifecycleState,
+}) => {
+	switch (lifecycleState) {
+		case "start_error":
+			return <ErrorScriptButton />;
+		case "start_timeout":
+			return <TimeoutScriptButton />;
+		default:
+			return null;
+	}
+};
+
+type StartupWarningButtonBaseProps = {
+	label: string;
+	errorMessage: string;
+};
+
+const StartupWarningButtonBase: FC<StartupWarningButtonBaseProps> = ({
+	label,
+	errorMessage,
+}) => {
+	return (
+		<TooltipProvider delayDuration={250}>
+			<Tooltip>
+				<TooltipTrigger asChild>
+					<Button
+						variant="outline"
+						size="sm"
+						className="border-amber-500 text-amber-600 dark:border-amber-600 dark:text-amber-400"
+					>
+						<TriangleAlertIcon />
+						{label}
+					</Button>
+				</TooltipTrigger>
+				<TooltipContent className="max-w-sm bg-surface-secondary p-4">
+					<p className="m-0 text-sm font-normal text-content-primary leading-snug">
+						A workspace{" "}
+						<Link
+							href={docs(
+								"/admin/templates/troubleshooting#startup-script-exited-with-an-error",
+							)}
+							target="_blank"
+							rel="noreferrer"
+						>
+							{errorMessage}
+						</Link>
+						. We recommend{" "}
+						<Link
+							href={docs(
+								"/admin/templates/troubleshooting#startup-script-issues",
+							)}
+							target="_blank"
+							rel="noreferrer"
+						>
+							debugging the startup script
+						</Link>{" "}
+						because{" "}
+						<Link
+							href={docs(
+								"/admin/templates/troubleshooting#your-workspace-may-be-incomplete",
+							)}
+							target="_blank"
+							rel="noreferrer"
+						>
+							your workspace may be incomplete
+						</Link>
+						.
+					</p>
+				</TooltipContent>
+			</Tooltip>
+		</TooltipProvider>
+	);
+};
+
+const ErrorScriptButton: FC = () => {
+	return (
+		<StartupWarningButtonBase
+			label="Startup Error"
+			errorMessage="startup script has exited with an error"
+		/>
+	);
+};
+
+const TimeoutScriptButton: FC = () => {
+	return (
+		<StartupWarningButtonBase
+			label="Startup Timeout"
+			errorMessage="startup script has timed out"
+		/>
+	);
+};
diff --git a/site/src/pages/TaskPage/TaskTopbar.tsx b/site/src/pages/TaskPage/TaskTopbar.tsx
index 3d22631ae14b8..b5affcbfffe0b 100644
--- a/site/src/pages/TaskPage/TaskTopbar.tsx
+++ b/site/src/pages/TaskPage/TaskTopbar.tsx
@@ -16,6 +16,7 @@ import {
 } from "lucide-react";
 import type { FC } from "react";
 import { Link as RouterLink } from "react-router";
+import { TaskStartupWarningButton } from "./TaskStartupWarningButton";
 import { TaskStatusLink } from "./TaskStatusLink";
 
 type TaskTopbarProps = { task: Task; workspace: Workspace };
@@ -46,6 +47,10 @@ export const TaskTopbar: FC<TaskTopbarProps> = ({ task, workspace }) => {
 			)}
 
 			<div className="ml-auto gap-2 flex items-center">
+				<TaskStartupWarningButton
+					lifecycleState={task.workspace_agent_lifecycle}
+				/>
+
 				<TooltipProvider delayDuration={250}>
 					<Tooltip>
 						<TooltipTrigger asChild>