diff --git a/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.stories.tsx b/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.stories.tsx
index d6a2fbcf82..1af2905904 100644
--- a/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.stories.tsx
+++ b/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.stories.tsx
@@ -1,5 +1,5 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
-import { expect, spyOn, userEvent, within } from "storybook/test";
+import { expect, spyOn, userEvent, waitFor, within } from "storybook/test";
 import {
 	reactRouterOutlet,
 	reactRouterParameters,
@@ -73,13 +73,15 @@ export const EnablingAutostopUsesTemplateDefault: Story = {
 	},
 };
 
-export const ChangingAutostopShowsRestartDialog: Story = {
+export const EnablingAutostopShowsRestartDialog: Story = {
 	parameters: {
-		reactRouter: workspaceRouterParameters(MockWorkspace),
-		queries: workspaceQueries(MockWorkspace),
+		reactRouter: workspaceRouterParameters(autostopDisabledWorkspace),
+		queries: workspaceQueries(autostopDisabledWorkspace),
 	},
 	beforeEach: () => {
-		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(MockWorkspace);
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			autostopDisabledWorkspace,
+		);
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
@@ -94,19 +96,94 @@ export const ChangingAutostopShowsRestartDialog: Story = {
 	},
 };
 
-const stoppedWorkspace: Workspace = {
-	...MockWorkspace,
-	latest_build: { ...MockWorkspaceBuild, status: "stopped" },
-};
-
-export const ChangingAutostopWhileStoppedSkipsDialog: Story = {
+export const ApplyLaterKeepsUserOnSchedulePage: Story = {
 	parameters: {
-		reactRouter: workspaceRouterParameters(stoppedWorkspace),
-		queries: workspaceQueries(stoppedWorkspace),
+		reactRouter: workspaceRouterParameters(autostopDisabledWorkspace),
+		queries: workspaceQueries(autostopDisabledWorkspace),
 	},
 	beforeEach: () => {
 		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
-			stoppedWorkspace,
+			autostopDisabledWorkspace,
+		);
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const body = within(document.body);
+		const user = userEvent.setup();
+		const restartSpy = spyOn(API, "restartWorkspace");
+		await user.click(await canvas.findByLabelText("Enable Autostop"));
+		await user.click(await canvas.findByRole("button", { name: /save/i }));
+		await body.findByText("Restart workspace?");
+		await user.click(await body.findByRole("button", { name: /apply later/i }));
+		// The dialog closes without restarting or leaving the schedule page.
+		await waitFor(() =>
+			expect(body.queryByText("Restart workspace?")).not.toBeInTheDocument(),
+		);
+		expect(restartSpy).not.toHaveBeenCalled();
+		await canvas.findByLabelText("Enable Autostop");
+	},
+};
+
+export const ChangingAutostopValueShowsRestartDialog: Story = {
+	parameters: {
+		reactRouter: workspaceRouterParameters(MockWorkspace),
+		queries: workspaceQueries(MockWorkspace),
+	},
+	beforeEach: () => {
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(MockWorkspace);
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const body = within(document.body);
+		const user = userEvent.setup();
+		const ttlInput = await canvas.findByLabelText(
+			"Time until shutdown (hours)",
+		);
+		await user.clear(ttlInput);
+		await user.type(ttlInput, "4");
+		await user.click(await canvas.findByRole("button", { name: /save/i }));
+		await body.findByText(
+			`Schedule for workspace "${MockWorkspace.name}" updated successfully.`,
+		);
+		await body.findByText("Restart workspace?");
+	},
+};
+
+export const DisablingAutostopSkipsRestartDialog: Story = {
+	parameters: {
+		reactRouter: workspaceRouterParameters(MockWorkspace),
+		queries: workspaceQueries(MockWorkspace),
+	},
+	beforeEach: () => {
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(MockWorkspace);
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const body = within(document.body);
+		const user = userEvent.setup();
+		// MockWorkspace has autostop enabled, so clicking the toggle disables it.
+		await user.click(await canvas.findByLabelText("Enable Autostop"));
+		await user.click(await canvas.findByRole("button", { name: /save/i }));
+		await body.findByText(
+			`Schedule for workspace "${MockWorkspace.name}" updated successfully.`,
+		);
+		expect(body.queryByText("Restart workspace?")).not.toBeInTheDocument();
+	},
+};
+
+const stoppedAutostopDisabledWorkspace: Workspace = {
+	...autostopDisabledWorkspace,
+	latest_build: { ...MockWorkspaceBuild, status: "stopped" },
+};
+
+export const EnablingAutostopWhileStoppedSkipsDialog: Story = {
+	parameters: {
+		reactRouter: workspaceRouterParameters(stoppedAutostopDisabledWorkspace),
+		queries: workspaceQueries(stoppedAutostopDisabledWorkspace),
+	},
+	beforeEach: () => {
+		spyOn(API, "getWorkspaceByOwnerAndName").mockResolvedValue(
+			stoppedAutostopDisabledWorkspace,
 		);
 	},
 	play: async ({ canvasElement }) => {
diff --git a/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.tsx b/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.tsx
index 68c2ab0fd3..91fda3f556 100644
--- a/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.tsx
+++ b/site/src/pages/WorkspaceSettingsPage/WorkspaceSchedulePage/WorkspaceSchedulePage.tsx
@@ -140,9 +140,19 @@ const WorkspaceSchedulePage: FC = () => {
 
 							await submitScheduleMutation.mutateAsync(data);
 
+							// A running build's autostop deadline is calculated when the
+							// build starts, so updating the TTL does not retroactively
+							// change it. Prompt the user to restart so the new value takes
+							// effect immediately, but only when all of the following hold:
+							//   - autostop actually changed (toggled or new TTL value),
+							//   - autostop is enabled after the change; disabling clears the
+							//     running build's deadline server-side, so no restart is
+							//     needed, and
+							//   - the workspace is running; a stopped workspace picks up the
+							//     new value on its next start.
 							if (
 								data.autostopChanged &&
-								getAutostop(workspace).autostopEnabled &&
+								values.autostopEnabled &&
 								workspace.latest_build.status === "running"
 							) {
 								setIsConfirmingApply(true);
@@ -163,7 +173,9 @@ const WorkspaceSchedulePage: FC = () => {
 					navigate(`/@${username}/${workspaceName}`);
 				}}
 				onClose={() => {
-					navigate(`/@${username}/${workspaceName}`);
+					// Keep the user on the schedule page; the saved value still
+					// applies on the next workspace start.
+					setIsConfirmingApply(false);
 				}}
 			/>
 		</div>