diff --git a/webui/src/App.tsx b/webui/src/App.tsx
index 55f94fb7c..9746e73f6 100644
--- a/webui/src/App.tsx
+++ b/webui/src/App.tsx
@@ -43,7 +43,7 @@ import type {
 } from "@/lib/types";
 import { Button } from "@/components/ui/button";
 import { Input } from "@/components/ui/input";
-import { fetchSettings, fetchWorkspaces } from "@/lib/api";
+import { fetchSessionAutomations, fetchSettings, fetchWorkspaces } from "@/lib/api";
 import {
   createRuntimeHost,
   getHostApi,
@@ -548,7 +548,6 @@ function Shell({
     key: string;
     label: string;
     automations?: SessionAutomationJob[];
-    confirmAutomations?: boolean;
   } | null>(null);
   const [pendingRename, setPendingRename] = useState<{
     key: string;
@@ -1273,6 +1272,7 @@ function Shell({
   const onConfirmDelete = useCallback(async () => {
     if (!pendingDelete) return;
     const key = pendingDelete.key;
+    const hasAutomations = (pendingDelete.automations?.length ?? 0) > 0;
     const deletingActive = activeKey === key;
     const currentIndex = sessions.findIndex((s) => s.key === key);
     const fallbackKey = deletingActive
@@ -1281,13 +1281,12 @@ function Shell({
     try {
       const result = await deleteChat(
         key,
-        pendingDelete.confirmAutomations ? { deleteAutomations: true } : undefined,
+        hasAutomations ? { deleteAutomations: true } : undefined,
       );
       if (result.blocked_by_automations) {
         setPendingDelete({
           ...pendingDelete,
           automations: result.automations ?? [],
-          confirmAutomations: true,
         });
         return;
       }
@@ -1304,6 +1303,16 @@ function Shell({
     }
   }, [pendingDelete, deleteChat, activeKey, navigate, sessions]);
 
+  const onRequestDelete = useCallback(async (key: string, label: string) => {
+    let automations: SessionAutomationJob[] = [];
+    try {
+      automations = (await fetchSessionAutomations(token, key)).jobs;
+    } catch {
+      // Delete remains protected by the backend block; prefetch only improves the first prompt.
+    }
+    setPendingDelete({ key, label, automations });
+  }, [token]);
+
   const headerTitle = activeSession
     ? sidebarState.title_overrides[activeSession.key] ||
       activeSession.title ||
@@ -1340,8 +1349,7 @@ function Shell({
     loading,
     onNewChat,
     onSelect: onSelectChat,
-    onRequestDelete: (key: string, label: string) =>
-      setPendingDelete({ key, label }),
+    onRequestDelete,
     onTogglePin,
     onRequestRename,
     onToggleArchive,
@@ -1566,7 +1574,7 @@ function Shell({
         <DeleteConfirm
           open={!!pendingDelete}
           title={pendingDelete?.label ?? ""}
-          automations={pendingDelete?.confirmAutomations ? pendingDelete.automations : undefined}
+          automations={pendingDelete?.automations}
           onCancel={() => setPendingDelete(null)}
           onConfirm={onConfirmDelete}
         />
diff --git a/webui/src/tests/app-layout.test.tsx b/webui/src/tests/app-layout.test.tsx
index 8735fa00b..9e39688ba 100644
--- a/webui/src/tests/app-layout.test.tsx
+++ b/webui/src/tests/app-layout.test.tsx
@@ -146,8 +146,9 @@ vi.mock("@/hooks/useSessions", async (importOriginal) => {
         refresh: refreshSpy,
         createChat: createChatSpy,
         forkChat: async () => "fork-chat",
-        deleteChat: async (key: string) => {
-          await deleteChatSpy(key);
+        deleteChat: async (key: string, options?: { deleteAutomations?: boolean }) => {
+          if (options === undefined) await deleteChatSpy(key);
+          else await deleteChatSpy(key, options);
           setSessions((prev: ChatSummary[]) => prev.filter((s) => s.key !== key));
           return { deleted: true };
         },
@@ -434,6 +435,73 @@ describe("App layout", () => {
     expect(document.body.style.pointerEvents).not.toBe("none");
   }, 15_000);
 
+  it("shows bound automations in the first delete confirmation", async () => {
+    mockSessions = [
+      {
+        key: "websocket:chat-a",
+        channel: "websocket",
+        chatId: "chat-a",
+        createdAt: "2026-04-16T10:00:00Z",
+        updatedAt: "2026-04-16T10:00:00Z",
+        preview: "First chat",
+      },
+      {
+        key: "websocket:chat-b",
+        channel: "websocket",
+        chatId: "chat-b",
+        createdAt: "2026-04-16T11:00:00Z",
+        updatedAt: "2026-04-16T11:00:00Z",
+        preview: "Second chat",
+      },
+    ];
+    mockFetchRoutes({
+      "/api/sessions/websocket%3Achat-a/automations": {
+        jobs: [
+          {
+            id: "job-1",
+            name: "Daily repo check",
+            enabled: true,
+            schedule: { kind: "every", every_ms: 86_400_000 },
+            payload: { message: "Check the repo" },
+            state: { next_run_at_ms: Date.UTC(2026, 3, 17, 10, 0, 0) },
+          },
+        ],
+      },
+    });
+
+    render(<App />);
+
+    await waitFor(() => expect(connectSpy).toHaveBeenCalled());
+    const sidebar = screen.getByRole("navigation", { name: "Sidebar navigation" });
+    await waitFor(() =>
+      expect(
+        within(sidebar).getByRole("button", { name: /^First chat$/ }),
+      ).toBeInTheDocument(),
+    );
+
+    fireEvent.pointerDown(screen.getByLabelText("Chat actions for First chat"), {
+      button: 0,
+    });
+    fireEvent.click(await screen.findByRole("menuitem", { name: "Delete" }));
+
+    await waitFor(() =>
+      expect(screen.getByText("Daily repo check")).toBeInTheDocument(),
+    );
+    expect(
+      screen.getByText("This chat has scheduled automations. Deleting it will also delete them."),
+    ).toBeInTheDocument();
+
+    fireEvent.click(screen.getByRole("button", { name: "Delete chat and automations" }));
+
+    await waitFor(() =>
+      expect(deleteChatSpy).toHaveBeenCalledWith("websocket:chat-a", {
+        deleteAutomations: true,
+      }),
+    );
+    expect(deleteChatSpy).toHaveBeenCalledTimes(1);
+    expect(screen.queryByText("Daily repo check")).not.toBeInTheDocument();
+  }, 15_000);
+
   it("keeps the mobile session action menu inside the sidebar sheet", async () => {
     mockSessions = [
       {