diff --git a/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx b/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx
index 121f619847..f7370b960e 100644
--- a/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx
+++ b/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx
@@ -1,4 +1,5 @@
 import { memo, useEffect, useId, useLayoutEffect, useMemo, useRef, useState } from 'react';
+import { Loader2, AlertCircle } from 'lucide-react';
 import { Tools } from 'librechat-data-provider';
 import type { TAttachment, TFile, TAttachmentMetadata } from 'librechat-data-provider';
 import type { ToolArtifactType } from '~/utils/artifacts';
@@ -18,11 +19,50 @@ import Image from '~/components/Chat/Messages/Content/Image';
 import ToolMermaidArtifact from './ToolMermaidArtifact';
 import ToolArtifactCard from './ToolArtifactCard';
 import { useAttachmentLink } from './LogLink';
-import { useLocalize } from '~/hooks';
+import { useLocalize, useAttachmentPreviewSync } from '~/hooks';
 import { cn } from '~/utils';
 
 const COLLAPSED_MAX_HEIGHT = 320;
 
+/**
+ * Small inline indicator rendered next to a code-execution file chip
+ * while its inline preview is in flight or has failed. Three states:
+ *
+ *  - `'pending'`: tiny spinner + "preparing preview…". Driven by the
+ *    polling `useAttachmentPreviewSync` hook (gated on `isSubmitting`)
+ *    and by the SSE `attachment` update event when the response stream
+ *    is still open.
+ *  - `'failed'`: alert icon + "preview unavailable" with the
+ *    backend's machine-readable `previewError` as a tooltip
+ *    (`'timeout'`, `'parser-error'`, `'orphaned'`, …). The download
+ *    chip itself remains fully functional.
+ *  - `'ready'` (or undefined): nothing rendered — the chip looks
+ *    exactly as it did before this PR.
+ */
+const PreviewStatusIndicator = memo(
+  ({ status, previewError }: { status: 'pending' | 'failed'; previewError?: string }) => {
+    const localize = useLocalize();
+    if (status === 'pending') {
+      return (
+        <div className="mt-1 flex items-center gap-1.5 text-xs text-text-secondary">
+          <Loader2 className="h-3 w-3 animate-spin" aria-hidden="true" />
+          <span>{localize('com_ui_preview_preparing')}</span>
+        </div>
+      );
+    }
+    return (
+      <div
+        className="mt-1 flex items-center gap-1.5 text-xs text-text-secondary"
+        title={previewError ?? localize('com_ui_preview_failed')}
+      >
+        <AlertCircle className="h-3 w-3" aria-hidden="true" />
+        <span>{localize('com_ui_preview_failed')}</span>
+      </div>
+    );
+  },
+);
+PreviewStatusIndicator.displayName = 'PreviewStatusIndicator';
+
 const FileAttachment = memo(({ attachment }: { attachment: Partial<TAttachment> }) => {
   const [isVisible, setIsVisible] = useState(false);
   const file = attachment as TFile & TAttachmentMetadata;
@@ -34,6 +74,14 @@ const FileAttachment = memo(({ attachment }: { attachment: Partial<TAttachment>
     source: file.source,
   });
   const extension = attachment.filename?.split('.').pop();
+  /* Bridge the two-phase preview lifecycle: poll the backend for the
+   * resolved record while pending+isSubmitting, and surface a small
+   * UI indicator. The hook is a no-op for terminal states (legacy
+   * records, ready, failed already-known) so calling it
+   * unconditionally is cheap. */
+  const { status: previewStatus, previewError } = useAttachmentPreviewSync(
+    attachment as TAttachment,
+  );
 
   useEffect(() => {
     const timer = setTimeout(() => setIsVisible(true), 50);
@@ -64,6 +112,9 @@ const FileAttachment = memo(({ attachment }: { attachment: Partial<TAttachment>
         containerClassName="max-w-fit"
         buttonClassName="bg-surface-secondary hover:cursor-pointer hover:bg-surface-hover active:bg-surface-secondary focus:bg-surface-hover hover:border-border-heavy active:border-border-heavy"
       />
+      {(previewStatus === 'pending' || previewStatus === 'failed') && (
+        <PreviewStatusIndicator status={previewStatus} previewError={previewError} />
+      )}
     </div>
   );
 });
diff --git a/client/src/data-provider/Files/queries.ts b/client/src/data-provider/Files/queries.ts
index 9a213d5ad1..6430889908 100644
--- a/client/src/data-provider/Files/queries.ts
+++ b/client/src/data-provider/Files/queries.ts
@@ -105,3 +105,41 @@ export const useCodeOutputDownload = (url = ''): QueryObserverResult<string> =>
     },
   );
 };
+
+/**
+ * Poll the lifecycle of an inline file preview while phase-2 HTML
+ * extraction runs in the background.
+ *
+ * Caller wires `enabled` to `(attachment.status === 'pending') && isSubmitting`
+ * so the query is dormant for terminal-status records and stops the
+ * moment the assistant finishes generating. Once enabled, React Query's
+ * `refetchInterval` runs at 2.5s while the server keeps returning
+ * `'pending'`, then auto-stops on the first `'ready'`/`'failed'`
+ * response (returning `false` from the function form disables the
+ * interval). Idle by default.
+ *
+ * Cache key: `[QueryKeys.filePreview, file_id]`. Sibling components
+ * watching the same `file_id` get a single shared poller.
+ */
+export const useFilePreview = (
+  file_id: string | undefined,
+  config?: UseQueryOptions<t.TFilePreview, unknown, t.TFilePreview>,
+): QueryObserverResult<t.TFilePreview, unknown> => {
+  return useQuery<t.TFilePreview, unknown, t.TFilePreview>(
+    [QueryKeys.filePreview, file_id],
+    () => dataService.getFilePreview(file_id ?? ''),
+    {
+      refetchOnWindowFocus: false,
+      refetchOnReconnect: false,
+      refetchOnMount: false,
+      retry: false,
+      /* Function form: poll only while the server says 'pending'.
+       * Returning `false` disables the interval, so a single 'ready'
+       * or 'failed' response naturally terminates polling without the
+       * caller having to also flip `enabled`. */
+      refetchInterval: (data) => (data?.status === 'pending' ? 2500 : false),
+      ...config,
+      enabled: !!file_id && (config?.enabled ?? true),
+    },
+  );
+};
diff --git a/client/src/hooks/Files/__tests__/useAttachmentPreviewSync.spec.tsx b/client/src/hooks/Files/__tests__/useAttachmentPreviewSync.spec.tsx
new file mode 100644
index 0000000000..6c0aa40538
--- /dev/null
+++ b/client/src/hooks/Files/__tests__/useAttachmentPreviewSync.spec.tsx
@@ -0,0 +1,235 @@
+/**
+ * Coverage for `useAttachmentPreviewSync` — the bridge between the
+ * two-phase code-execution preview lifecycle and the attachment cache.
+ *
+ * Behavior under test:
+ *   1. Polling enables only when `attachment.status === 'pending'` AND
+ *      some conversation is submitting (per the user's explicit gate).
+ *   2. On a terminal poll response (ready/failed), the resolved record
+ *      is upserted into `messageAttachmentsMap` by `file_id`.
+ *   3. The hook's returned `status` reflects the polled value once
+ *      it arrives, not just the prop snapshot.
+ *
+ * The underlying `useFilePreview` hook is mocked here — its own
+ * polling cadence and refetchInterval semantics are React Query's
+ * concern, not this hook's.
+ */
+
+import { renderHook } from '@testing-library/react';
+import { RecoilRoot, useRecoilValue, useSetRecoilState } from 'recoil';
+import type { ReactNode } from 'react';
+import type { TAttachment, TFilePreview } from 'librechat-data-provider';
+import store from '~/store';
+
+const mockUseFilePreview = jest.fn();
+jest.mock('~/data-provider', () => ({
+  useFilePreview: (...args: unknown[]) => mockUseFilePreview(...args),
+}));
+
+import useAttachmentPreviewSync from '../useAttachmentPreviewSync';
+
+const wrapper = ({ children }: { children: ReactNode }) => <RecoilRoot>{children}</RecoilRoot>;
+
+const messageId = 'msg-1';
+const fileId = 'fid-1';
+
+function makeAttachment(overrides: Partial<TAttachment> = {}): TAttachment {
+  return {
+    file_id: fileId,
+    filename: 'data.xlsx',
+    filepath: '/uploads/data.xlsx',
+    type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',
+    messageId,
+    toolCallId: 'tc-1',
+    text: null,
+    textFormat: null,
+    status: 'pending',
+    ...overrides,
+  } as unknown as TAttachment;
+}
+
+/** Read messageAttachmentsMap and bridge it out via a mutable ref. */
+function setup({
+  attachment,
+  isSubmitting,
+  preview,
+  isFetching = false,
+}: {
+  attachment: TAttachment;
+  isSubmitting: boolean;
+  preview?: TFilePreview;
+  isFetching?: boolean;
+}) {
+  mockUseFilePreview.mockReset();
+  mockUseFilePreview.mockReturnValue({ data: preview, isFetching });
+  const ref: { current: Record<string, TAttachment[] | undefined> } = { current: {} };
+  let lastEnabled: boolean | undefined;
+  /* Spy on the second arg of useFilePreview to assert the gate. */
+  mockUseFilePreview.mockImplementation((_id: unknown, opts: { enabled?: boolean }) => {
+    lastEnabled = opts?.enabled;
+    return { data: preview, isFetching };
+  });
+
+  const Bridge = () => {
+    /* Seed the messageAttachmentsMap with the test attachment so the
+     * hook's upsert path has something to find. Also expose setters
+     * for tests that simulate `isAnySubmitting` toggling — the
+     * selector reads `conversationKeysAtom` × `isSubmittingFamily(key)`
+     * so we have to populate both for the selector to fire. */
+    const setMap = useSetRecoilState(store.messageAttachmentsMap);
+    if (Object.keys(ref.current).length === 0) {
+      setMap({ [messageId]: [attachment] });
+    }
+    const setKeys = useSetRecoilState(store.conversationKeysAtom);
+    setKeys([0]);
+    const setSubmitting = useSetRecoilState(store.isSubmittingFamily(0));
+    setSubmitting(isSubmitting);
+    const map = useRecoilValue(store.messageAttachmentsMap);
+    ref.current = map;
+    return null;
+  };
+
+  const { result } = renderHook(
+    () => {
+      return useAttachmentPreviewSync(attachment);
+    },
+    {
+      wrapper: ({ children }: { children: ReactNode }) =>
+        wrapper({
+          children: (
+            <>
+              <Bridge />
+              {children}
+            </>
+          ),
+        }),
+    },
+  );
+
+  return {
+    result,
+    get map() {
+      return ref.current;
+    },
+    get enabled() {
+      return lastEnabled;
+    },
+  };
+}
+
+describe('useAttachmentPreviewSync', () => {
+  it('enables polling only when status=pending AND a conversation is submitting', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: true,
+    });
+    expect(ctx.enabled).toBe(true);
+  });
+
+  it('does NOT enable polling when status is already ready', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'ready' }),
+      isSubmitting: true,
+    });
+    expect(ctx.enabled).toBe(false);
+  });
+
+  it('does NOT enable polling when status is already failed', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'failed', previewError: 'timeout' }),
+      isSubmitting: true,
+    });
+    expect(ctx.enabled).toBe(false);
+  });
+
+  it('does NOT enable polling when no conversation is submitting (LLM finished)', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: false,
+    });
+    /* User's explicit gate: once the LLM is done, polling stops. The
+     * frontend can refetch on demand from the next interaction. */
+    expect(ctx.enabled).toBe(false);
+  });
+
+  it('does NOT enable polling when the attachment has no file_id', () => {
+    const noId = { ...makeAttachment({ status: 'pending' }) } as Partial<TAttachment>;
+    delete (noId as { file_id?: string }).file_id;
+    const ctx = setup({
+      attachment: noId as TAttachment,
+      isSubmitting: true,
+    });
+    expect(ctx.enabled).toBe(false);
+  });
+
+  it('returns ready when no preview and no status (legacy back-compat)', () => {
+    const legacy = makeAttachment();
+    delete (legacy as Partial<TAttachment & { status?: string }>).status;
+    const ctx = setup({ attachment: legacy as TAttachment, isSubmitting: false });
+    expect(ctx.result.current.status).toBe('ready');
+  });
+
+  it('upserts the resolved preview into messageAttachmentsMap when phase-2 reports ready', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: true,
+      preview: {
+        file_id: fileId,
+        status: 'ready',
+        text: '<table>final</table>',
+        textFormat: 'html',
+      },
+    });
+    const updated = ctx.map[messageId]?.[0] as TAttachment & { text?: string };
+    expect(updated.status).toBe('ready');
+    expect(updated.text).toBe('<table>final</table>');
+    expect(ctx.result.current.status).toBe('ready');
+  });
+
+  it('upserts the resolved preview when phase-2 reports failed (with previewError)', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: true,
+      preview: {
+        file_id: fileId,
+        status: 'failed',
+        previewError: 'parser-error',
+      },
+    });
+    const updated = ctx.map[messageId]?.[0] as TAttachment & { previewError?: string };
+    expect(updated.status).toBe('failed');
+    expect(updated.previewError).toBe('parser-error');
+    expect(ctx.result.current.status).toBe('failed');
+    expect(ctx.result.current.previewError).toBe('parser-error');
+  });
+
+  it('does NOT upsert while the polled status is still pending', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: true,
+      preview: { file_id: fileId, status: 'pending' },
+    });
+    /* Map should be unchanged from the initial seed — no patch. */
+    const list = ctx.map[messageId] ?? [];
+    expect(list).toHaveLength(1);
+    expect((list[0] as TAttachment & { status?: string }).status).toBe('pending');
+  });
+
+  it('reports isPolling true when the query is fetching and the gate is open', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: true,
+      isFetching: true,
+    });
+    expect(ctx.result.current.isPolling).toBe(true);
+  });
+
+  it('reports isPolling false when the query is not fetching', () => {
+    const ctx = setup({
+      attachment: makeAttachment({ status: 'pending' }),
+      isSubmitting: true,
+      isFetching: false,
+    });
+    expect(ctx.result.current.isPolling).toBe(false);
+  });
+});
diff --git a/client/src/hooks/Files/index.ts b/client/src/hooks/Files/index.ts
index 499572f0e0..7fa4df5a17 100644
--- a/client/src/hooks/Files/index.ts
+++ b/client/src/hooks/Files/index.ts
@@ -1,3 +1,4 @@
+export { default as useAttachmentPreviewSync } from './useAttachmentPreviewSync';
 export { default as useDeleteFilesFromTable } from './useDeleteFilesFromTable';
 export { default as useSetFilesToDelete } from './useSetFilesToDelete';
 export { default as useFileHandling, useFileHandlingNoChatContext } from './useFileHandling';
diff --git a/client/src/hooks/Files/useAttachmentPreviewSync.ts b/client/src/hooks/Files/useAttachmentPreviewSync.ts
new file mode 100644
index 0000000000..0134b018ed
--- /dev/null
+++ b/client/src/hooks/Files/useAttachmentPreviewSync.ts
@@ -0,0 +1,108 @@
+import { useEffect } from 'react';
+import { useRecoilValue, useSetRecoilState } from 'recoil';
+import type { TAttachment, TFile, TFilePreview } from 'librechat-data-provider';
+import { useFilePreview } from '~/data-provider';
+import store from '~/store';
+
+interface UseAttachmentPreviewSyncResult {
+  /**
+   * Effective lifecycle status: `'pending'` while phase-2 HTML
+   * extraction is in flight, `'ready'` once it completes successfully
+   * (or for legacy / non-office files that never had a status), and
+   * `'failed'` when extraction errored or hit the 60s ceiling. Drives
+   * UI state (spinner, badge, etc.) without callers needing to read
+   * the attachment shape directly.
+   */
+  status: 'pending' | 'ready' | 'failed';
+  /** Short machine-readable failure reason from the backend. */
+  previewError?: string;
+  /** True while React Query is actively polling the preview endpoint. */
+  isPolling: boolean;
+}
+
+/**
+ * Bridge the two-phase code-execution preview lifecycle to the
+ * attachment cache.
+ *
+ * Phase-1 (handled in callbacks.js + processCodeOutput) emits the
+ * attachment record at `status: 'pending'` immediately so the agent's
+ * response stops blocking on extraction. Phase-2 runs in the
+ * background; if the SSE stream is still open when it lands, an
+ * `attachment` update event arrives and the SSE handler upserts by
+ * `file_id`. If the stream has already closed (the model finished
+ * generating before phase-2 resolved), this hook covers the gap by
+ * polling `GET /api/files/:file_id/preview` and writing the resolved
+ * record back into `messageAttachmentsMap` — which triggers
+ * re-classification through `artifactTypeForAttachment`, so the file
+ * chip transitions from a plain download to the rich preview card
+ * (or to a download-with-error state) without remounting.
+ *
+ * Polling is gated on:
+ *   - `attachment.file_id` present (no id → nothing to poll for)
+ *   - Effective status is `'pending'` (terminal states need no work)
+ *   - Some conversation in the app is submitting (per the user's
+ *     explicit gate: "only query when the preview is still live and
+ *     `isSubmitting` is still true"). When the LLM finishes, polling
+ *     stops; the user can refresh on demand from the next interaction.
+ */
+export default function useAttachmentPreviewSync(
+  attachment: TAttachment | undefined,
+): UseAttachmentPreviewSyncResult {
+  const setAttachmentsMap = useSetRecoilState(store.messageAttachmentsMap);
+  const isAnySubmitting = useRecoilValue(store.anySubmittingSelector);
+
+  const file = (attachment ?? undefined) as Partial<TFile> | undefined;
+  const fileId = file?.file_id;
+  const baseStatus: 'pending' | 'ready' | 'failed' = file?.status ?? 'ready';
+  const messageId = (attachment as Partial<TAttachment> | undefined)?.messageId;
+
+  const enabled = !!fileId && baseStatus === 'pending' && isAnySubmitting;
+
+  const previewQuery = useFilePreview(fileId, { enabled });
+
+  /* Effective status: prefer the polled record once it arrives, since
+   * the SSE handler may have already moved the cache forward and the
+   * `attachment` prop will catch up on the next render anyway. */
+  const polled = previewQuery.data as TFilePreview | undefined;
+  const effectiveStatus: 'pending' | 'ready' | 'failed' = polled?.status ?? baseStatus;
+  const previewError = polled?.previewError ?? file?.previewError;
+
+  /* On a terminal poll response (ready or failed), upsert into the
+   * shared attachments map. Mirrors the SSE handler's by-file_id
+   * upsert (`useAttachmentHandler`) — the attachment object is
+   * patched in place so siblings sharing the same atom re-render
+   * with the resolved data and `artifactTypeForAttachment` re-runs
+   * its empty-text gate, transitioning the file chip into a panel
+   * artifact card. */
+  useEffect(() => {
+    if (!polled || polled.status === 'pending' || !messageId || !fileId) {
+      return;
+    }
+    setAttachmentsMap((prevMap) => {
+      const messageAttachments =
+        (prevMap as Record<string, TAttachment[] | undefined>)[messageId] || [];
+      const existingIndex = messageAttachments.findIndex(
+        (a) => (a as Partial<TFile>).file_id === fileId,
+      );
+      if (existingIndex < 0) {
+        return prevMap;
+      }
+      const existing = messageAttachments[existingIndex] as Partial<TFile> & TAttachment;
+      const merged = [...messageAttachments];
+      merged[existingIndex] = {
+        ...existing,
+        status: polled.status,
+        text: polled.text ?? existing.text ?? null,
+        textFormat: polled.textFormat ?? existing.textFormat ?? null,
+        previewError: polled.previewError,
+      } as TAttachment;
+      return { ...prevMap, [messageId]: merged };
+    });
+  }, [polled, fileId, messageId, setAttachmentsMap]);
+
+  return {
+    status: effectiveStatus,
+    previewError,
+    isPolling: enabled && previewQuery.isFetching,
+  };
+}
diff --git a/client/src/hooks/SSE/__tests__/useAttachmentHandler.spec.tsx b/client/src/hooks/SSE/__tests__/useAttachmentHandler.spec.tsx
new file mode 100644
index 0000000000..42f211ba52
--- /dev/null
+++ b/client/src/hooks/SSE/__tests__/useAttachmentHandler.spec.tsx
@@ -0,0 +1,148 @@
+/**
+ * Coverage for the upsert-by-file_id behavior in `useAttachmentHandler`.
+ *
+ * Two-phase code-execution flow: phase-1 emits an attachment with
+ * `status: 'pending'`; phase-2 emits the same `file_id` again with
+ * `status: 'ready'` (and resolved `text`/`textFormat`) or
+ * `'failed'` (with `previewError`). The handler MUST merge over the
+ * pending placeholder in place — appending would render the artifact
+ * twice in the UI (once stuck pending, once resolved).
+ *
+ * Lightweight attachments without a `file_id` (web_search citations,
+ * file_search results) keep the legacy append-only behavior so two
+ * unrelated citations both show up.
+ */
+
+import { renderHook, act } from '@testing-library/react';
+import { RecoilRoot, useRecoilValue } from 'recoil';
+import { QueryClient } from '@tanstack/react-query';
+import { Tools } from 'librechat-data-provider';
+import type { ReactNode } from 'react';
+import type { TAttachment, EventSubmission } from 'librechat-data-provider';
+import useAttachmentHandler from '../useAttachmentHandler';
+import store from '~/store';
+
+const wrapper = ({ children }: { children: ReactNode }) => <RecoilRoot>{children}</RecoilRoot>;
+
+const submission = {} as EventSubmission;
+const messageId = 'msg-1';
+
+function makeAttachment(overrides: Partial<TAttachment>): TAttachment {
+  return {
+    file_id: 'fid-1',
+    filename: 'data.xlsx',
+    filepath: '/uploads/data.xlsx',
+    type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',
+    messageId,
+    toolCallId: 'tc-1',
+    text: null,
+    textFormat: null,
+    status: 'pending',
+    ...overrides,
+  } as unknown as TAttachment;
+}
+
+/* Co-mount the handler and a reader of the messageAttachmentsMap atom in
+ * the same RecoilRoot so each act() shows the post-write state. The
+ * `attachmentsMap` ref is mutated by the reader on every render, so
+ * callers read it after their `act()` to assert. */
+function setup() {
+  const queryClient = new QueryClient();
+  const ref: { current: Record<string, TAttachment[] | undefined> } = { current: {} };
+  const { result } = renderHook(
+    () => {
+      const handler = useAttachmentHandler(queryClient);
+      const map = useRecoilValue(store.messageAttachmentsMap);
+      ref.current = map;
+      return handler;
+    },
+    { wrapper },
+  );
+  return {
+    handle: (data: TAttachment) => act(() => result.current({ data, submission })),
+    get list(): TAttachment[] {
+      return ref.current[messageId] ?? [];
+    },
+  };
+}
+
+describe('useAttachmentHandler upsert-by-file_id', () => {
+  it('appends a new attachment when no record with the same file_id exists', () => {
+    const ctx = setup();
+    ctx.handle(makeAttachment({ status: 'pending' }));
+    expect(ctx.list).toHaveLength(1);
+    expect(ctx.list[0]).toMatchObject({ file_id: 'fid-1', status: 'pending' });
+  });
+
+  it('upserts in place when a second event arrives for the same file_id (phase-1 → phase-2 ready)', () => {
+    const ctx = setup();
+    ctx.handle(makeAttachment({ status: 'pending' }));
+    ctx.handle(makeAttachment({ status: 'ready', text: '<table></table>', textFormat: 'html' }));
+    /* Critical: still ONE attachment, not two. The phase-2 event
+     * patches the pending record in place. */
+    expect(ctx.list).toHaveLength(1);
+    expect(ctx.list[0]).toMatchObject({
+      file_id: 'fid-1',
+      status: 'ready',
+      text: '<table></table>',
+      textFormat: 'html',
+    });
+  });
+
+  it('upserts a failed phase-2 over the pending placeholder', () => {
+    const ctx = setup();
+    ctx.handle(makeAttachment({ status: 'pending' }));
+    ctx.handle(makeAttachment({ status: 'failed', previewError: 'timeout' }));
+    expect(ctx.list).toHaveLength(1);
+    expect(ctx.list[0]).toMatchObject({ status: 'failed', previewError: 'timeout' });
+  });
+
+  it('keeps multiple distinct file_ids as separate entries', () => {
+    const ctx = setup();
+    ctx.handle(makeAttachment({ file_id: 'fid-A' }));
+    ctx.handle(makeAttachment({ file_id: 'fid-B' }));
+    expect(ctx.list).toHaveLength(2);
+    expect(ctx.list.map((a) => (a as { file_id: string }).file_id).sort()).toEqual([
+      'fid-A',
+      'fid-B',
+    ]);
+  });
+
+  it('appends (does NOT merge) attachments with no file_id', () => {
+    /* Lightweight attachments like file_search citations and web_search
+     * results don't carry file_id. The handler must keep its legacy
+     * append behavior for them — merging would lose distinct citations
+     * and is unnecessary because they're never the target of a phase-2
+     * update. */
+    const ctx = setup();
+    const noFileId = {
+      messageId,
+      toolCallId: 'tc-1',
+      type: Tools.web_search,
+    } as unknown as TAttachment;
+    ctx.handle(noFileId);
+    ctx.handle(noFileId);
+    expect(ctx.list).toHaveLength(2);
+  });
+
+  it('preserves fields from the first event when the second omits them', () => {
+    /* Phase-2 update only carries the deltas (text, status, textFormat).
+     * Fields set in phase-1 (filename, type, etc.) must survive the
+     * merge — the second event uses spread-over-existing semantics. */
+    const ctx = setup();
+    ctx.handle(makeAttachment({ status: 'pending', filename: 'phase1-name.xlsx' }));
+    ctx.handle({
+      file_id: 'fid-1',
+      messageId,
+      status: 'ready',
+      text: 'final',
+      textFormat: 'html',
+    } as unknown as TAttachment);
+    expect(ctx.list).toHaveLength(1);
+    expect(ctx.list[0]).toMatchObject({
+      filename: 'phase1-name.xlsx',
+      status: 'ready',
+      text: 'final',
+    });
+  });
+});
diff --git a/client/src/hooks/SSE/useAttachmentHandler.ts b/client/src/hooks/SSE/useAttachmentHandler.ts
index 06261f4af6..d4a03c3d41 100644
--- a/client/src/hooks/SSE/useAttachmentHandler.ts
+++ b/client/src/hooks/SSE/useAttachmentHandler.ts
@@ -52,6 +52,26 @@ export default function useAttachmentHandler(queryClient?: QueryClient) {
     setAttachmentsMap((prevMap) => {
       const messageAttachments =
         (prevMap as Record<string, TAttachment[] | undefined>)[messageId] || [];
+      /* Upsert by `file_id` rather than always appending. The two-phase
+       * code-execution flow emits the same attachment twice: once at
+       * phase-1 with `status: 'pending'` and `text: null`, then again
+       * at phase-2 with `status: 'ready'` (and text/textFormat) or
+       * `'failed'` (with previewError). The second event must merge
+       * over the first in place — appending would render the artifact
+       * card twice, once stuck pending and once resolved. Attachments
+       * without a `file_id` (lightweight types like web_search /
+       * file_search citations) keep the legacy append behavior. */
+      const fileId = (data as Partial<TFile>).file_id;
+      if (fileId) {
+        const existingIndex = messageAttachments.findIndex(
+          (a) => (a as Partial<TFile>).file_id === fileId,
+        );
+        if (existingIndex > -1) {
+          const merged = [...messageAttachments];
+          merged[existingIndex] = { ...messageAttachments[existingIndex], ...data };
+          return { ...prevMap, [messageId]: merged };
+        }
+      }
       return {
         ...prevMap,
         [messageId]: [...messageAttachments, data],
diff --git a/client/src/locales/en/translation.json b/client/src/locales/en/translation.json
index efeaced119..60d68b8d79 100644
--- a/client/src/locales/en/translation.json
+++ b/client/src/locales/en/translation.json
@@ -1304,6 +1304,8 @@
   "com_ui_prev": "Prev",
   "com_ui_prev_result": "Previous result",
   "com_ui_preview": "Preview",
+  "com_ui_preview_failed": "Preview unavailable",
+  "com_ui_preview_preparing": "Preparing preview…",
   "com_ui_preview_unavailable": "Preview not available for this file type",
   "com_ui_privacy_policy": "Privacy policy",
   "com_ui_privacy_policy_url": "Privacy Policy URL",
diff --git a/packages/data-provider/src/api-endpoints.ts b/packages/data-provider/src/api-endpoints.ts
index 992d4a78a6..8bd38427fe 100644
--- a/packages/data-provider/src/api-endpoints.ts
+++ b/packages/data-provider/src/api-endpoints.ts
@@ -284,6 +284,11 @@ export const fileUpload = () => `${BASE_URL}/api/files`;
 export const fileDelete = () => `${BASE_URL}/api/files`;
 export const fileDownload = (userId: string, fileId: string) =>
   `${BASE_URL}/api/files/download/${userId}/${fileId}`;
+/* Two-phase code-execution preview lifecycle endpoint. Returns
+ * `{ status, text?, textFormat?, previewError? }` so the frontend can
+ * poll while phase-2 HTML extraction is in flight. See PR #12952. */
+export const filePreview = (fileId: string) =>
+  `${BASE_URL}/api/files/${encodeURIComponent(fileId)}/preview`;
 export const fileConfig = () => `${BASE_URL}/api/files/config`;
 export const agentFiles = (agentId: string) => `${BASE_URL}/api/files/agent/${agentId}`;
 
diff --git a/packages/data-provider/src/data-service.ts b/packages/data-provider/src/data-service.ts
index 1e118c6f07..45f6ca6fdb 100644
--- a/packages/data-provider/src/data-service.ts
+++ b/packages/data-provider/src/data-service.ts
@@ -402,6 +402,22 @@ export const getFiles = (): Promise<f.TFile[]> => {
   return request.get(endpoints.files());
 };
 
+/**
+ * Poll the lifecycle of an inline file preview. Returns the smallest
+ * shape needed to drive the UI:
+ *   - `status` always present (defaults to `'ready'` server-side for
+ *     legacy records that pre-date the field).
+ *   - `text` and `textFormat` only when `status === 'ready'` and text
+ *     was extracted (preserves the HTML-or-null security contract).
+ *   - `previewError` only when `status === 'failed'`.
+ *
+ * Called from `useFilePreview` with React Query's `refetchInterval`
+ * gated on `status === 'pending'` and `isSubmitting`. See PR #12952.
+ */
+export const getFilePreview = (fileId: string): Promise<f.TFilePreview> => {
+  return request.get(endpoints.filePreview(fileId));
+};
+
 export const getAgentFiles = (agentId: string): Promise<f.TFile[]> => {
   return request.get(endpoints.agentFiles(agentId));
 };
diff --git a/packages/data-provider/src/keys.ts b/packages/data-provider/src/keys.ts
index 2200558cf1..36f4286617 100644
--- a/packages/data-provider/src/keys.ts
+++ b/packages/data-provider/src/keys.ts
@@ -34,6 +34,7 @@ export enum QueryKeys {
   assistantDocs = 'assistantDocs',
   agentDocs = 'agentDocs',
   fileDownload = 'fileDownload',
+  filePreview = 'filePreview',
   voices = 'voices',
   customConfigSpeech = 'customConfigSpeech',
   prompts = 'prompts',