diff --git a/client/src/hooks/Files/__tests__/useFileDeletion.spec.tsx b/client/src/hooks/Files/__tests__/useFileDeletion.spec.tsx
new file mode 100644
index 0000000000..da084426c8
--- /dev/null
+++ b/client/src/hooks/Files/__tests__/useFileDeletion.spec.tsx
@@ -0,0 +1,135 @@
+import React, { useState } from 'react';
+import { FileSources, EToolResources } from 'librechat-data-provider';
+import { render, screen, act, renderHook } from '@testing-library/react';
+import type { ExtendedFile } from '~/common';
+import FileRow from '~/components/Chat/Input/Files/FileRow';
+import useFileDeletion from '../useFileDeletion';
+
+const mockMutateAsync = jest.fn();
+
+jest.mock('~/data-provider', () => ({
+  useDeleteFilesMutation: () => ({ mutateAsync: mockMutateAsync }),
+}));
+
+jest.mock('@librechat/client', () => ({
+  useToastContext: () => ({ showToast: jest.fn() }),
+}));
+
+jest.mock('~/hooks', () => ({
+  useLocalize: () => (key: string) => key,
+}));
+
+jest.mock('~/utils', () => ({
+  ...jest.requireActual('~/utils'),
+  logger: { log: jest.fn() },
+  getCachedPreview: () => undefined,
+  deletePreview: jest.fn(),
+}));
+
+jest.mock('../useSetFilesToDelete', () => ({
+  __esModule: true,
+  default: () => jest.fn(),
+}));
+
+jest.mock('~/components/Chat/Input/Files/FileContainer', () => {
+  return function MockFileContainer({
+    file,
+    onDelete,
+  }: {
+    file: ExtendedFile;
+    onDelete: () => void;
+  }) {
+    return <button data-testid={`del-${file.file_id}`} onClick={onDelete} />;
+  };
+});
+
+jest.mock('~/components/Chat/Input/Files/Image', () => {
+  return function MockImage() {
+    return null;
+  };
+});
+
+/** Mirrors the shape `utils/forms.tsx` builds for agent Context/File Search panels */
+const makeFile = (file_id: string): ExtendedFile =>
+  ({
+    file_id,
+    type: 'application/pdf',
+    filepath: `/uploads/${file_id}.pdf`,
+    filename: `${file_id}.pdf`,
+    size: 1024,
+    progress: 1,
+    source: FileSources.local,
+  }) as ExtendedFile;
+
+/** Mirrors FileContext.tsx, which mounts FileRow only while `fileCount > 0` */
+function ConditionalPanel({ initial }: { initial: ExtendedFile[] }) {
+  const [files, setFiles] = useState(new Map(initial.map((f) => [f.file_id, f])));
+  return (
+    <>
+      {files.size > 0 && (
+        <FileRow
+          files={files}
+          setFiles={setFiles}
+          agent_id="agent-123"
+          tool_resource={EToolResources.context}
+        />
+      )}
+    </>
+  );
+}
+
+describe('useFileDeletion', () => {
+  beforeEach(() => {
+    jest.useFakeTimers();
+    mockMutateAsync.mockClear();
+  });
+  afterEach(() => jest.useRealTimers());
+
+  const clickDelete = (file_id: string) => {
+    act(() => {
+      screen.getByTestId(`del-${file_id}`).click();
+    });
+    act(() => {
+      jest.advanceTimersByTime(3000);
+    });
+  };
+
+  it('sends the unlink request when removing the last file from an agent panel', () => {
+    render(<ConditionalPanel initial={[makeFile('only-file')]} />);
+
+    clickDelete('only-file');
+
+    expect(mockMutateAsync).toHaveBeenCalledTimes(1);
+    expect(mockMutateAsync).toHaveBeenCalledWith({
+      files: [expect.objectContaining({ file_id: 'only-file' })],
+      agent_id: 'agent-123',
+      tool_resource: EToolResources.context,
+    });
+  });
+
+  it('sends the unlink request when removing a non-last file from an agent panel', () => {
+    render(<ConditionalPanel initial={[makeFile('file-a'), makeFile('file-b')]} />);
+
+    clickDelete('file-a');
+
+    expect(mockMutateAsync).toHaveBeenCalledTimes(1);
+    expect(mockMutateAsync).toHaveBeenCalledWith(
+      expect.objectContaining({ agent_id: 'agent-123', tool_resource: EToolResources.context }),
+    );
+  });
+
+  it('does not delete a file that was attached from existing storage', () => {
+    const { result } = renderHook(() => useFileDeletion({ mutateAsync: mockMutateAsync }));
+
+    act(() => {
+      result.current.deleteFile({
+        file: { ...makeFile('stored-file'), attached: true } as ExtendedFile,
+      });
+    });
+    act(() => {
+      jest.advanceTimersByTime(3000);
+    });
+
+    expect(mockMutateAsync).not.toHaveBeenCalled();
+  });
+});
diff --git a/client/src/hooks/Files/useFileDeletion.ts b/client/src/hooks/Files/useFileDeletion.ts
index c33ac2a50b..18a189b9ac 100644
--- a/client/src/hooks/Files/useFileDeletion.ts
+++ b/client/src/hooks/Files/useFileDeletion.ts
@@ -1,8 +1,8 @@
+import { useCallback, useState, useEffect } from 'react';
 import debounce from 'lodash/debounce';
 import { FileSources, EToolResources, removeNullishValues } from 'librechat-data-provider';
-import { useCallback, useState, useEffect } from 'react';
-import type * as t from 'librechat-data-provider';
 import type { UseMutateAsyncFunction } from '@tanstack/react-query';
+import type * as t from 'librechat-data-provider';
 import type { ExtendedFile, GenericSetter } from '~/common';
 import useSetFilesToDelete from './useSetFilesToDelete';
 import { deletePreview } from '~/utils';
@@ -51,8 +51,9 @@ const useFileDeletion = ({
   const debouncedDelete = useCallback(debounce(executeBatchDelete, 1000), []);
 
   useEffect(() => {
-    // Cleanup function for debouncedDelete when component unmounts or before re-render
-    return () => debouncedDelete.cancel();
+    /** Flush, don't cancel: unmount is a normal outcome of removing the last file,
+     * and a cancelled batch silently drops a delete the user already confirmed. */
+    return () => debouncedDelete.flush();
   }, [debouncedDelete]);
 
   const deleteFile = useCallback(