diff --git a/coderd/workspaces.go b/coderd/workspaces.go
index 87aea6919a351..6f398b34488d6 100644
--- a/coderd/workspaces.go
+++ b/coderd/workspaces.go
@@ -1052,6 +1052,18 @@ func (api *API) putExtendWorkspace(rw http.ResponseWriter, r *http.Request) {
 			return xerrors.Errorf("workspace shutdown is manual")
 		}
 
+		tmpl, err := s.GetTemplateByID(ctx, workspace.TemplateID)
+		if err != nil {
+			code = http.StatusInternalServerError
+			resp.Message = "Error fetching template."
+			return xerrors.Errorf("get template: %w", err)
+		}
+		if !tmpl.AllowUserAutostop {
+			code = http.StatusBadRequest
+			resp.Message = "Cannot extend workspace: template does not allow user autostop."
+			return xerrors.New("cannot extend workspace: template does not allow user autostop")
+		}
+
 		newDeadline := req.Deadline.UTC()
 		if err := validWorkspaceDeadline(job.CompletedAt.Time, newDeadline); err != nil {
 			// NOTE(Cian): Putting the error in the Message field on request from the FE folks.
diff --git a/enterprise/coderd/workspaces_test.go b/enterprise/coderd/workspaces_test.go
index b44357c5b5dde..9cb86f55ba55f 100644
--- a/enterprise/coderd/workspaces_test.go
+++ b/enterprise/coderd/workspaces_test.go
@@ -913,8 +913,12 @@ func TestWorkspaceAutobuild(t *testing.T) {
 		ws = coderdtest.MustWorkspace(t, client, ws.ID)
 		require.Equal(t, version2.ID, ws.LatestBuild.TemplateVersionID)
 	})
+}
+
+func TestTemplateDoesNotAllowUserAutostop(t *testing.T) {
+	t.Parallel()
 
-	t.Run("TemplateDoesNotAllowUserAutostop", func(t *testing.T) {
+	t.Run("TTLSetByTemplate", func(t *testing.T) {
 		t.Parallel()
 		client := coderdtest.New(t, &coderdtest.Options{
 			IncludeProvisionerDaemon: true,
@@ -951,6 +955,34 @@ func TestWorkspaceAutobuild(t *testing.T) {
 		require.Equal(t, templateTTL, template.DefaultTTLMillis)
 		require.Equal(t, templateTTL, *workspace.TTLMillis)
 	})
+
+	t.Run("ExtendIsNotEnabledByTemplate", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, &coderdtest.Options{
+			IncludeProvisionerDaemon: true,
+			TemplateScheduleStore:    schedule.NewEnterpriseTemplateScheduleStore(agplUserQuietHoursScheduleStore()),
+		})
+		user := coderdtest.CreateFirstUser(t, client)
+		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID, func(ctr *codersdk.CreateTemplateRequest) {
+			ctr.AllowUserAutostop = ptr.Ref(false)
+		})
+		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+		workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
+		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
+
+		require.Equal(t, false, template.AllowUserAutostop, "template should have AllowUserAutostop as false")
+
+		ctx := testutil.Context(t, testutil.WaitShort)
+		ttl := 8 * time.Hour
+		newDeadline := time.Now().Add(ttl + time.Hour).UTC()
+
+		err := client.PutExtendWorkspace(ctx, workspace.ID, codersdk.PutExtendWorkspaceRequest{
+			Deadline: newDeadline,
+		})
+
+		require.ErrorContains(t, err, "template does not allow user autostop")
+	})
 }
 
 // Blocked by autostart requirements
diff --git a/site/src/pages/WorkspacePage/WorkspaceTopbar.stories.tsx b/site/src/pages/WorkspacePage/WorkspaceTopbar.stories.tsx
index 8b0334b1dccfc..1cf8eeec78a67 100644
--- a/site/src/pages/WorkspacePage/WorkspaceTopbar.stories.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceTopbar.stories.tsx
@@ -275,3 +275,21 @@ export const WithQuota: Story = {
     ],
   },
 };
+
+export const TemplateDoesNotAllowAutostop: Story = {
+  args: {
+    workspace: {
+      ...MockWorkspace,
+      latest_build: {
+        ...MockWorkspace.latest_build,
+        get deadline() {
+          return addHours(new Date(), 8).toISOString();
+        },
+      },
+    },
+    template: {
+      ...MockTemplate,
+      allow_user_autostop: false,
+    },
+  },
+};
diff --git a/site/src/pages/WorkspacePage/WorkspaceTopbar.tsx b/site/src/pages/WorkspacePage/WorkspaceTopbar.tsx
index e2337fd8a0bd5..d05f7c7c66453 100644
--- a/site/src/pages/WorkspacePage/WorkspaceTopbar.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceTopbar.tsx
@@ -204,7 +204,9 @@ export const WorkspaceTopbar: FC<WorkspaceProps> = ({
           <WorkspaceScheduleControls
             workspace={workspace}
             template={template}
-            canUpdateSchedule={canUpdateWorkspace}
+            canUpdateSchedule={
+              canUpdateWorkspace && template.allow_user_autostop
+            }
           />
         )}