diff --git a/site/src/pages/TaskPage/FollowUpDialog.tsx b/site/src/pages/TaskPage/FollowUpDialog.tsx
new file mode 100644
index 0000000000..b09fc51459
--- /dev/null
+++ b/site/src/pages/TaskPage/FollowUpDialog.tsx
@@ -0,0 +1,95 @@
+import type { Task } from "api/typesGenerated";
+import { Button } from "components/Button/Button";
+import {
+	Dialog,
+	DialogClose,
+	DialogContent,
+	DialogDescription,
+	DialogFooter,
+	DialogHeader,
+	DialogTitle,
+} from "components/Dialog/Dialog";
+import { Textarea } from "components/Textarea/Textarea";
+import { useFormik } from "formik";
+import type { FC } from "react";
+import { useId } from "react";
+
+type FollowUpDialogProps = {
+	task: Task;
+	initialMessage: string;
+	open: boolean;
+	onOpenChange: (open: boolean) => void;
+	onSubmit: (message: string) => void;
+};
+
+export const FollowUpDialog: FC<FollowUpDialogProps> = ({
+	task,
+	initialMessage,
+	open,
+	onOpenChange,
+	onSubmit,
+}) => {
+	const formId = useId();
+
+	const formik = useFormik({
+		initialValues: {
+			message: initialMessage,
+		},
+		enableReinitialize: true,
+		onSubmit: (values) => {
+			const message = values.message.trim();
+			if (message.length === 0) {
+				return;
+			}
+			onSubmit(message);
+			onOpenChange(false);
+		},
+	});
+
+	return (
+		<Dialog open={open} onOpenChange={onOpenChange}>
+			<DialogContent className="max-w-2xl">
+				<DialogHeader>
+					<DialogTitle>Send Follow-up Message</DialogTitle>
+					<DialogDescription>
+						Add another message to this task. The task will resume and send this
+						follow-up automatically.
+					</DialogDescription>
+				</DialogHeader>
+
+				<form id={formId} className="space-y-4" onSubmit={formik.handleSubmit}>
+					<div>
+						<label
+							htmlFor={`${formId}-message`}
+							className="block text-sm font-medium text-content-primary mb-2"
+						>
+							Follow-up message
+						</label>
+						<Textarea
+							id={`${formId}-message`}
+							name="message"
+							value={formik.values.message}
+							onChange={formik.handleChange}
+							rows={10}
+							className="w-full"
+							placeholder={`Continue "${task.display_name}" after resume by asking for the next step...`}
+						/>
+					</div>
+				</form>
+
+				<DialogFooter>
+					<DialogClose asChild>
+						<Button variant="outline">Cancel</Button>
+					</DialogClose>
+					<Button
+						type="submit"
+						form={formId}
+						disabled={formik.values.message.trim().length === 0}
+					>
+						Send Follow-up
+					</Button>
+				</DialogFooter>
+			</DialogContent>
+		</Dialog>
+	);
+};
diff --git a/site/src/pages/TaskPage/TaskPage.stories.tsx b/site/src/pages/TaskPage/TaskPage.stories.tsx
index 6c2ecb9226..5ecf06fdeb 100644
--- a/site/src/pages/TaskPage/TaskPage.stories.tsx
+++ b/site/src/pages/TaskPage/TaskPage.stories.tsx
@@ -136,6 +136,22 @@ const MockTaskLogsResponse: TaskLogsResponse = {
 	snapshot_at: new Date(Date.now() - 3 * 24 * 60 * 60 * 1000).toISOString(),
 };
 
+const getFollowUpDialog = async (canvasElement: HTMLElement) => {
+	const body = within(canvasElement.ownerDocument.body);
+	const dialogs = await body.findAllByRole("dialog", {
+		name: /send follow-up message/i,
+	});
+	// Radix dialog content can linger during transitions; use the newest instance.
+	const dialog = dialogs.at(-1);
+	if (!dialog) {
+		throw new Error("Follow-up dialog was not found.");
+	}
+	return {
+		body,
+		dialog: within(dialog),
+	};
+};
+
 const meta: Meta<typeof TaskPage> = {
 	title: "pages/TaskPage",
 	component: TaskPage,
@@ -369,6 +385,311 @@ export const TaskPausedSnapshotTooltip: Story = {
 	},
 };
 
+export const TaskPausedWithFollowUpDialog: Story = {
+	beforeEach: () => {
+		spyOn(API, "getTask").mockResolvedValue({
+			...MockTask,
+			status: "paused",
+		});
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const followUpButton = await canvas.findByRole("button", {
+			name: /follow-up/i,
+		});
+		await userEvent.click(followUpButton);
+
+		const body = within(canvasElement.ownerDocument.body);
+		const dialogTitle = await body.findByText("Send Follow-up Message");
+		expect(dialogTitle).toBeInTheDocument();
+	},
+};
+
+export const TaskFollowUpAutoResumeSuccess: Story = {
+	beforeEach: () => {
+		let isTaskActive = false;
+		spyOn(API, "getTask").mockImplementation(async () => ({
+			...MockTask,
+			status: isTaskActive ? "active" : "paused",
+		}));
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+		spyOn(API, "sendTaskInput").mockImplementation(async () => {
+			if (!isTaskActive) {
+				throw {
+					...mockApiError({
+						message: "Task is paused",
+						detail: "Resume required before sending",
+					}),
+					status: 409,
+				};
+			}
+		});
+		spyOn(API, "resumeTask").mockImplementation(async () => {
+			isTaskActive = true;
+			return {
+				workspace_build: MockStartingWorkspace.latest_build,
+			};
+		});
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { dialog } = await getFollowUpDialog(canvasElement);
+		await userEvent.type(
+			await dialog.findByLabelText(/follow-up message/i),
+			"Continue from where you left off",
+		);
+		await userEvent.click(
+			await dialog.findByRole("button", { name: /send follow-up/i }),
+		);
+
+		await waitFor(() => {
+			expect(API.resumeTask).toHaveBeenCalled();
+			expect(API.sendTaskInput).toHaveBeenCalledTimes(1);
+		});
+	},
+};
+
+export const TaskFollowUpActiveTaskDirectSend: Story = {
+	beforeEach: () => {
+		spyOn(API, "getTask").mockResolvedValue({
+			...MockTask,
+			status: "active",
+		});
+		// Keep paused UI visible (for Follow-up button) while simulating an already-active task.
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+		spyOn(API, "sendTaskInput").mockResolvedValue();
+		spyOn(API, "resumeTask").mockResolvedValue({
+			workspace_build: MockWorkspace.latest_build,
+		});
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { dialog } = await getFollowUpDialog(canvasElement);
+		await userEvent.type(
+			await dialog.findByLabelText(/follow-up message/i),
+			"Please continue with the next step",
+		);
+		await userEvent.click(
+			await dialog.findByRole("button", { name: /send follow-up/i }),
+		);
+
+		await waitFor(() => {
+			expect(API.sendTaskInput).toHaveBeenCalledTimes(1);
+			expect(API.resumeTask).not.toHaveBeenCalled();
+		});
+	},
+};
+
+export const TaskFollowUpEmptyMessageDisabled: Story = {
+	beforeEach: () => {
+		spyOn(API, "getTask").mockResolvedValue({
+			...MockTask,
+			status: "paused",
+		});
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { dialog } = await getFollowUpDialog(canvasElement);
+		const submit = await dialog.findByRole("button", {
+			name: /send follow-up/i,
+		});
+		expect(submit).toBeDisabled();
+	},
+};
+
+export const TaskFollowUpShowsResumingProgress: Story = {
+	beforeEach: () => {
+		spyOn(API, "getTask").mockResolvedValue({
+			...MockTask,
+			status: "paused",
+		});
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+		// Keep resuming stage visible for assertions.
+		spyOn(API, "resumeTask").mockImplementation(() => new Promise(() => {}));
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { body, dialog } = await getFollowUpDialog(canvasElement);
+		const messageInput = await dialog.findByLabelText(/follow-up message/i);
+		await userEvent.type(messageInput, "Continue task");
+		await userEvent.click(
+			await dialog.findByRole("button", { name: /send follow-up/i }),
+		);
+
+		await waitFor(() => {
+			expect(
+				body.queryByRole("heading", { name: /send follow-up message/i }),
+			).not.toBeInTheDocument();
+			expect(canvas.getByText("Resuming task...")).toBeInTheDocument();
+			const pendingLabel = canvas.getByText(/Pending follow-up:/i);
+			expect(pendingLabel.parentElement).toHaveTextContent("Continue task");
+			expect(
+				canvas.getByText(/clears the pending follow-up message/i),
+			).toBeInTheDocument();
+		});
+	},
+};
+
+export const TaskFollowUpRetrySendFailure: Story = {
+	beforeEach: () => {
+		let isTaskActive = false;
+		spyOn(API, "getTask").mockImplementation(async () => ({
+			...MockTask,
+			status: isTaskActive ? "active" : "paused",
+		}));
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+		spyOn(API, "sendTaskInput").mockRejectedValue(
+			new Error("Failed to send message"),
+		);
+		spyOn(API, "resumeTask").mockImplementation(async () => {
+			isTaskActive = true;
+			return {
+				workspace_build: MockStartingWorkspace.latest_build,
+			};
+		});
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { dialog } = await getFollowUpDialog(canvasElement);
+		const messageInput = await dialog.findByLabelText(/follow-up message/i);
+		await userEvent.type(messageInput, "Please continue");
+		await userEvent.click(
+			await dialog.findByRole("button", { name: /send follow-up/i }),
+		);
+
+		await waitFor(() => {
+			expect(canvas.getByText("Failed to send message")).toBeInTheDocument();
+			const pendingLabel = canvas.getByText(/Pending follow-up:/i);
+			expect(pendingLabel.parentElement).toHaveTextContent("Please continue");
+			expect(
+				canvas.getByRole("button", { name: /follow-up/i }),
+			).toBeInTheDocument();
+		});
+	},
+};
+
+export const TaskFollowUpResumeBuildFailure: Story = {
+	beforeEach: () => {
+		let hasBuildFailed = false;
+		spyOn(API, "getTask").mockResolvedValue({
+			...MockTask,
+			status: "paused",
+		});
+		spyOn(API, "getWorkspaceByOwnerAndName").mockImplementation(async () => {
+			if (!hasBuildFailed) {
+				return MockStoppedWorkspace;
+			}
+			return {
+				...MockStoppedWorkspace,
+				latest_build: {
+					...MockStoppedWorkspace.latest_build,
+					status: "failed",
+				},
+			};
+		});
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+		spyOn(API, "resumeTask").mockImplementation(async () => {
+			hasBuildFailed = true;
+			return {
+				workspace_build: MockStartingWorkspace.latest_build,
+			};
+		});
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { dialog } = await getFollowUpDialog(canvasElement);
+		const messageInput = await dialog.findByLabelText(/follow-up message/i);
+		await userEvent.type(messageInput, "Continue task");
+		await userEvent.click(
+			await dialog.findByRole("button", { name: /send follow-up/i }),
+		);
+
+		await waitFor(() => {
+			expect(API.resumeTask).toHaveBeenCalled();
+		});
+		expect(await canvas.findByText("Task build failed")).toBeInTheDocument();
+		expect(
+			await canvas.findByText("Please check the logs for more details."),
+		).toBeInTheDocument();
+	},
+};
+
+export const TaskFollowUpNon409SendFailure: Story = {
+	beforeEach: () => {
+		spyOn(API, "getTask").mockResolvedValue({
+			...MockTask,
+			status: "active",
+		});
+		// Keep paused UI visible (for Follow-up button) while simulating active-task send behavior.
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			MockStoppedWorkspace,
+		);
+		spyOn(API, "getTaskLogs").mockResolvedValue(MockTaskLogsResponse);
+		spyOn(API, "sendTaskInput").mockRejectedValue(
+			new Error("Failed to send message"),
+		);
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		await userEvent.click(
+			await canvas.findByRole("button", { name: /follow-up/i }),
+		);
+		const { dialog } = await getFollowUpDialog(canvasElement);
+		const messageInput = await dialog.findByLabelText(/follow-up message/i);
+		await userEvent.type(messageInput, "Continue task");
+		await userEvent.click(
+			await dialog.findByRole("button", { name: /send follow-up/i }),
+		);
+
+		await waitFor(() => {
+			expect(canvas.getByText("Failed to send message")).toBeInTheDocument();
+			const pendingLabel = canvas.getByText(/Pending follow-up:/i);
+			expect(pendingLabel.parentElement).toHaveTextContent("Continue task");
+			expect(
+				canvas.getByRole("button", { name: /follow-up/i }),
+			).toBeInTheDocument();
+		});
+	},
+};
+
 export const TaskPausedTimeout: Story = {
 	beforeEach: () => {
 		spyOn(API, "getTask").mockResolvedValue({
diff --git a/site/src/pages/TaskPage/TaskPage.tsx b/site/src/pages/TaskPage/TaskPage.tsx
index aab6717668..3a5b8f9f9e 100644
--- a/site/src/pages/TaskPage/TaskPage.tsx
+++ b/site/src/pages/TaskPage/TaskPage.tsx
@@ -2,7 +2,10 @@ import { API } from "api/api";
 import { getErrorDetail, getErrorMessage, isApiError } from "api/errors";
 import { pauseTask, resumeTask, taskLogs } from "api/queries/tasks";
 import { template as templateQueryOptions } from "api/queries/templates";
-import { workspaceByOwnerAndName } from "api/queries/workspaces";
+import {
+	workspaceByOwnerAndName,
+	workspaceByOwnerAndNameKey,
+} from "api/queries/workspaces";
 import type {
 	Task,
 	TaskLogEntry,
@@ -37,6 +40,7 @@ import {
 	type PropsWithChildren,
 	type ReactNode,
 	useCallback,
+	useEffect,
 	useLayoutEffect,
 	useRef,
 	useState,
@@ -53,11 +57,19 @@ import {
 	getActiveTransitionStats,
 	WorkspaceBuildProgress,
 } from "../WorkspacePage/WorkspaceBuildProgress";
+import { FollowUpDialog } from "./FollowUpDialog";
 import { ModifyPromptDialog } from "./ModifyPromptDialog";
 import { TaskAppIFrame } from "./TaskAppIframe";
 import { TaskApps } from "./TaskApps";
 import { TaskTopbar } from "./TaskTopbar";
 
+type FollowUpStage =
+	| "idle"
+	| "resuming"
+	| "waitingForActive"
+	| "sending"
+	| "error";
+
 const TaskPageLayout: FC<PropsWithChildren> = ({ children }) => {
 	return (
 		<div className="flex items-stretch h-full">
@@ -69,10 +81,29 @@ const TaskPageLayout: FC<PropsWithChildren> = ({ children }) => {
 
 const TaskPage = () => {
 	const [isModifyDialogOpen, setIsModifyDialogOpen] = useState(false);
+	const [isFollowUpDialogOpen, setIsFollowUpDialogOpen] = useState(false);
+	const [followUpDraft, setFollowUpDraft] = useState("");
+	const [followUpStage, setFollowUpStage] = useState<FollowUpStage>("idle");
+	const [followUpError, setFollowUpError] = useState<string>();
 	const { taskId, username } = useParams() as {
 		taskId: string;
 		username: string;
 	};
+	const taskRouteKey = `${username}/${taskId}`;
+	const prevTaskRouteKeyRef = useRef(taskRouteKey);
+	const queryClient = useQueryClient();
+	const resumeFollowUpMutation = useMutation({
+		mutationFn: () => API.resumeTask(username, taskId),
+		onSuccess: async () => {
+			await queryClient.invalidateQueries({ queryKey: ["tasks"] });
+		},
+	});
+	const sendFollowUpMutation = useMutation({
+		mutationFn: (input: string) => API.sendTaskInput(username, taskId, input),
+		onSuccess: async () => {
+			await queryClient.invalidateQueries({ queryKey: ["tasks"] });
+		},
+	});
 	const { data: task, ...taskQuery } = useQuery({
 		queryKey: ["tasks", username, taskId],
 		queryFn: () => API.getTask(username, taskId),
@@ -91,6 +122,116 @@ const TaskPage = () => {
 	const error = taskQuery.error ?? workspaceQuery.error;
 	const waitingStatuses: WorkspaceStatus[] = ["starting", "pending"];
 
+	useEffect(() => {
+		if (prevTaskRouteKeyRef.current === taskRouteKey) {
+			return;
+		}
+		prevTaskRouteKeyRef.current = taskRouteKey;
+		// Reset in-memory follow-up state when navigating to another task route.
+		setFollowUpDraft("");
+		setFollowUpStage("idle");
+		setFollowUpError(undefined);
+	}, [taskRouteKey]);
+
+	const startSendingFollowUp = useCallback(
+		async (message: string) => {
+			setFollowUpStage("sending");
+			try {
+				await sendFollowUpMutation.mutateAsync(message);
+				setFollowUpDraft("");
+				setFollowUpError(undefined);
+				setFollowUpStage("idle");
+			} catch (error) {
+				setFollowUpError(getErrorMessage(error, "Failed to send message."));
+				setFollowUpStage("error");
+			}
+		},
+		[sendFollowUpMutation],
+	);
+
+	const queueFollowUp = useCallback(
+		async (message: string) => {
+			const trimmedMessage = message.trim();
+			if (!trimmedMessage || !task || !workspace) {
+				return;
+			}
+
+			setFollowUpDraft(trimmedMessage);
+			setFollowUpError(undefined);
+
+			if (task.status === "active") {
+				void startSendingFollowUp(trimmedMessage);
+				return;
+			}
+
+			if (
+				followUpStage === "resuming" ||
+				followUpStage === "waitingForActive" ||
+				followUpStage === "sending"
+			) {
+				return;
+			}
+
+			setFollowUpStage("resuming");
+			try {
+				await resumeFollowUpMutation.mutateAsync();
+				await queryClient.invalidateQueries({
+					queryKey: ["tasks", task.owner_name, task.id],
+				});
+				await queryClient.invalidateQueries({
+					queryKey: workspaceByOwnerAndNameKey(
+						workspace.owner_name,
+						workspace.name,
+					),
+				});
+				setFollowUpStage("waitingForActive");
+			} catch (error) {
+				setFollowUpError(getErrorMessage(error, "Failed to resume task."));
+				setFollowUpStage("error");
+			}
+		},
+		[
+			followUpStage,
+			queryClient,
+			resumeFollowUpMutation,
+			startSendingFollowUp,
+			task,
+			workspace,
+		],
+	);
+
+	const openFollowUpDialog = useCallback(() => {
+		setIsFollowUpDialogOpen(true);
+	}, []);
+
+	useEffect(() => {
+		if (followUpStage !== "resuming" && followUpStage !== "waitingForActive") {
+			return;
+		}
+		if (
+			workspace?.latest_build.status === "failed" ||
+			workspace?.latest_build.status === "canceled"
+		) {
+			setFollowUpError(
+				"Failed to resume task because the workspace build did not complete successfully.",
+			);
+			setFollowUpStage("error");
+		}
+	}, [followUpStage, workspace?.latest_build.status]);
+
+	useEffect(() => {
+		// Only auto-send a queued follow-up after we explicitly entered the
+		// waiting stage and the task transitions back to active.
+		if (
+			!followUpDraft ||
+			task?.status !== "active" ||
+			followUpStage !== "waitingForActive"
+		) {
+			return;
+		}
+		void startSendingFollowUp(followUpDraft);
+	}, [followUpDraft, followUpStage, startSendingFollowUp, task?.status]);
+
 	if (error) {
 		return (
 			<TaskPageLayout>
@@ -159,6 +300,10 @@ const TaskPage = () => {
 				task={task}
 				workspace={workspace}
 				onEditPrompt={() => setIsModifyDialogOpen(true)}
+				onAddFollowUp={openFollowUpDialog}
+				followUpDraft={followUpDraft}
+				followUpStage={followUpStage}
+				followUpError={followUpError}
 			/>
 		);
 	} else if (workspace.latest_build.status === "canceling") {
@@ -225,6 +370,15 @@ const TaskPage = () => {
 				open={isModifyDialogOpen}
 				onOpenChange={setIsModifyDialogOpen}
 			/>
+			<FollowUpDialog
+				task={task}
+				initialMessage={followUpDraft}
+				open={isFollowUpDialogOpen}
+				onOpenChange={setIsFollowUpDialogOpen}
+				onSubmit={(message) => {
+					void queueFollowUp(message);
+				}}
+			/>
 		</TaskPageLayout>
 	);
 };
@@ -437,9 +591,21 @@ type TaskPausedProps = {
 	task: Task;
 	workspace: Workspace;
 	onEditPrompt: () => void;
+	onAddFollowUp: () => void;
+	followUpDraft: string;
+	followUpStage: FollowUpStage;
+	followUpError?: string;
 };
 
-const TaskPaused: FC<TaskPausedProps> = ({ task, workspace, onEditPrompt }) => {
+const TaskPaused: FC<TaskPausedProps> = ({
+	task,
+	workspace,
+	onEditPrompt,
+	onAddFollowUp,
+	followUpDraft,
+	followUpStage,
+	followUpError,
+}) => {
 	const queryClient = useQueryClient();
 
 	// Use mutation config directly to customize error handling:
@@ -470,6 +636,17 @@ const TaskPaused: FC<TaskPausedProps> = ({ task, workspace, onEditPrompt }) => {
 	const apiError = isApiError(resumeMutation.error)
 		? resumeMutation.error
 		: undefined;
+	const hasPendingFollowUp = followUpDraft.trim().length > 0;
+	const isFollowUpSending =
+		followUpStage === "resuming" ||
+		followUpStage === "waitingForActive" ||
+		followUpStage === "sending";
+	const followUpStatusLabels: Record<string, string> = {
+		resuming: "Resuming task...",
+		waitingForActive: "Waiting for the task to become active...",
+		sending: "Sending follow-up message...",
+	};
+	const followUpStatusLabel = followUpStatusLabels[followUpStage];
 
 	return (
 		<>
@@ -494,18 +671,51 @@ const TaskPaused: FC<TaskPausedProps> = ({ task, workspace, onEditPrompt }) => {
 					)
 				}
 				actions={
-					<div className="flex flex-row gap-4">
-						<Button
-							size="sm"
-							disabled={isWaitingForStart}
-							onClick={() => resumeMutation.mutate()}
-						>
-							<Spinner loading={isWaitingForStart} />
-							Resume
-						</Button>
-						<Button size="sm" onClick={onEditPrompt} variant="outline">
-							Edit prompt
-						</Button>
+					<div className="flex flex-col gap-3 items-center">
+						<div className="flex flex-row gap-4">
+							<Button
+								size="sm"
+								disabled={isWaitingForStart}
+								onClick={() => resumeMutation.mutate()}
+							>
+								<Spinner loading={isWaitingForStart} />
+								Resume
+							</Button>
+							<Button size="sm" variant="outline" onClick={onEditPrompt}>
+								Edit prompt
+							</Button>
+							<Button size="sm" variant="outline" onClick={onAddFollowUp}>
+								Follow-up
+							</Button>
+						</div>
+
+						{hasPendingFollowUp && (
+							<div className="w-full max-w-xl rounded-md border border-border p-3 text-left text-sm">
+								<p className="m-0 text-content-primary">
+									<strong>Pending follow-up:</strong> {followUpDraft}
+								</p>
+								{followUpStatusLabel && (
+									<p className="m-0 mt-2 text-content-secondary flex items-center gap-2">
+										<Spinner loading />
+										{followUpStatusLabel}
+									</p>
+								)}
+								{followUpError && (
+									<p className="m-0 mt-2 text-content-destructive">
+										{followUpError}
+									</p>
+								)}
+								<p className="m-0 mt-2 text-content-secondary">
+									Refreshing or leaving this page clears the pending follow-up
+									message.
+								</p>
+							</div>
+						)}
+						{!hasPendingFollowUp && isFollowUpSending && (
+							<p className="m-0 text-content-secondary text-sm">
+								<Spinner loading /> Processing follow-up message...
+							</p>
+						)}
 					</div>
 				}
 			/>
@@ -517,7 +727,7 @@ const TaskPaused: FC<TaskPausedProps> = ({ task, workspace, onEditPrompt }) => {
 						<Button
 							size="sm"
 							variant="subtle"
-							disabled={isWaitingForStart}
+							disabled={isWaitingForStart || isFollowUpSending}
 							onClick={() => resumeMutation.mutate()}
 						>
 							<Spinner loading={isWaitingForStart} />