diff --git a/app/src/lib/attachments.test.ts b/app/src/lib/attachments.test.ts
index 4323ac9a1..4b67e1378 100644
--- a/app/src/lib/attachments.test.ts
+++ b/app/src/lib/attachments.test.ts
@@ -256,6 +256,41 @@ describe('parseMessageImages', () => {
     expect(result.text).toBe('');
     expect(result.dataUris).toHaveLength(1);
   });
+
+  it('strips FILE markers without including them in dataUris', () => {
+    const result = parseMessageImages('read this [FILE:data:application/pdf;base64,xyz]');
+    expect(result.text).toBe('read this');
+    expect(result.dataUris).toEqual([]);
+  });
+
+  it('handles mixed IMAGE and FILE markers', () => {
+    const result = parseMessageImages(
+      'check this [IMAGE:data:image/png;base64,a] and [FILE:data:application/pdf;base64,b] thanks'
+    );
+    expect(result.text).toBe('check this and thanks');
+    expect(result.dataUris).toEqual(['data:image/png;base64,a']);
+  });
+
+  it('strips multiple FILE markers', () => {
+    const result = parseMessageImages(
+      '[FILE:data:application/pdf;base64,a] [FILE:data:text/plain;base64,b]'
+    );
+    expect(result.text).toBe('');
+    expect(result.dataUris).toEqual([]);
+  });
+
+  it('preserves paragraph breaks (double newlines) in user text', () => {
+    const result = parseMessageImages('first paragraph\n\nsecond paragraph');
+    expect(result.text).toBe('first paragraph\n\nsecond paragraph');
+  });
+
+  it('preserves newlines when stripping a marker', () => {
+    const result = parseMessageImages(
+      'first paragraph\n\n[FILE:data:application/pdf;base64,x]\n\nsecond paragraph'
+    );
+    expect(result.text).toBe('first paragraph\n\n\n\nsecond paragraph');
+    expect(result.text).toContain('\n\n');
+  });
 });
 
 describe('formatFileSize', () => {
diff --git a/app/src/lib/attachments.ts b/app/src/lib/attachments.ts
index 4b6a92382..22395bd3a 100644
--- a/app/src/lib/attachments.ts
+++ b/app/src/lib/attachments.ts
@@ -247,8 +247,9 @@ export function buildMessageWithAttachments(text: string, attachments: Attachmen
 }
 
 /**
- * Parse `[IMAGE:<data-uri>]` markers out of a stored message string.
- * Returns the clean text (markers removed) and the list of data URIs found.
+ * Parse `[IMAGE:<data-uri>]` and `[FILE:<data-uri>]` markers out of a stored message string.
+ * Returns the clean text (markers removed) and the list of image data URIs found.
+ * File markers are stripped from text but not returned (file data lives in extraMetadata).
  */
 export function parseMessageImages(content: string): { text: string; dataUris: string[] } {
   const dataUris: string[] = [];
@@ -257,6 +258,11 @@ export function parseMessageImages(content: string): { text: string; dataUris: s
       dataUris.push(uri);
       return '';
     })
+    .replace(/\[FILE:([^\]]+)\]/g, '') // Strip file markers
+    // Collapse only runs of plain spaces (not \s) left behind by marker
+    // removal — using \s here would also eat intentional newlines/paragraph
+    // breaks in the user's own text.
+    .replace(/ {2,}/g, ' ')
     .trim();
   return { text, dataUris };
 }
diff --git a/app/src/pages/Conversations.tsx b/app/src/pages/Conversations.tsx
index e47860af1..3377868d4 100644
--- a/app/src/pages/Conversations.tsx
+++ b/app/src/pages/Conversations.tsx
@@ -1835,6 +1835,13 @@ const Conversations = ({
             )}
             {visibleMessages.map(msg => {
               const isAgentTextMode = msg.sender === 'agent' && agentMessageViewMode === 'text';
+              // Parsed once per message: for current messages (extraMetadata
+              // present, or agent messages) msg.content already has no markers,
+              // so this is a no-op. For legacy persisted user messages with raw
+              // [IMAGE:...]/[FILE:...] markers and no extraMetadata, this is
+              // what keeps the marker text out of both the rendered bubble and
+              // the copy-to-clipboard action.
+              const parsedContent = parseMessageImages(msg.content ?? '');
               return (
                 <div key={msg.id}>
                   <div
@@ -1893,9 +1900,10 @@ const Conversations = ({
                       ) : (
                         <div className="flex flex-col items-end gap-1">
                           {(() => {
+                            const displayText = parsedContent.text;
                             const dataUris = Array.isArray(msg.extraMetadata?.attachmentDataUris)
                               ? (msg.extraMetadata.attachmentDataUris as string[])
-                              : parseMessageImages(msg.content ?? '').dataUris;
+                              : parsedContent.dataUris;
                             const hasImages = dataUris.length > 0;
                             // Document attachments carry no image data-URI (only
                             // images do); surface them as filename chips from the
@@ -1953,14 +1961,14 @@ const Conversations = ({
                                     ))}
                                   </div>
                                 )}
-                                {(msg.content || showTime) && (
+                                {(displayText || showTime) && (
                                   <div className="rounded-2xl px-4 py-2.5 bg-primary-500 text-white rounded-br-md break-words overflow-hidden">
-                                    {msg.content && (
-                                      <BubbleMarkdown content={msg.content} tone="user" />
+                                    {displayText && (
+                                      <BubbleMarkdown content={displayText} tone="user" />
                                     )}
                                     {showTime && (
                                       <p
-                                        className={`${msg.content ? 'mt-1' : ''} text-[10px] text-white/60`}>
+                                        className={`${displayText ? 'mt-1' : ''} text-[10px] text-white/60`}>
                                         {formatRelativeTime(msg.createdAt)}
                                       </p>
                                     )}
@@ -1974,7 +1982,7 @@ const Conversations = ({
                       <button
                         type="button"
                         data-analytics-id="chat-message-copy"
-                        onClick={() => handleCopyMessage(msg.id, msg.content)}
+                        onClick={() => handleCopyMessage(msg.id, parsedContent.text)}
                         className={`absolute -top-1 ${
                           isAgentTextMode
                             ? 'right-0'
diff --git a/app/src/pages/__tests__/Conversations.attachments.test.tsx b/app/src/pages/__tests__/Conversations.attachments.test.tsx
index 4a8c7ab01..5a026260a 100644
--- a/app/src/pages/__tests__/Conversations.attachments.test.tsx
+++ b/app/src/pages/__tests__/Conversations.attachments.test.tsx
@@ -637,6 +637,73 @@ describe('Conversations — attachment feature', () => {
       expect(document.body.textContent).toContain('report.pdf');
     });
   });
+
+  it('strips raw IMAGE/FILE markers from a legacy message with no extraMetadata', async () => {
+    const writeText = vi.fn().mockResolvedValue(undefined);
+    Object.defineProperty(navigator, 'clipboard', { configurable: true, value: { writeText } });
+    const thread = makeThread({ id: 'legacy-thread', title: 'Legacy Thread' });
+    const dataUri = 'data:image/png;base64,legacy123';
+    const message = {
+      id: 'msg-legacy-1',
+      content: `read this [IMAGE:${dataUri}] and [FILE:data:application/pdf;base64,xyz]`,
+      type: 'text' as const,
+      sender: 'user' as const,
+      createdAt: new Date().toISOString(),
+      extraMetadata: {},
+    };
+
+    mockGetThreads.mockResolvedValue({ threads: [thread], count: 1 });
+    mockGetThreadMessages.mockResolvedValue({ messages: [message], count: 1 });
+
+    const store = buildStore({
+      thread: {
+        threads: [thread],
+        selectedThreadId: thread.id,
+        activeThreadIds: {},
+        welcomeThreadId: null,
+        messagesByThreadId: { [thread.id]: [message] },
+        messages: [message],
+        isLoadingThreads: false,
+        isLoadingMessages: false,
+        messagesError: null,
+      },
+      socket: socketState('connected'),
+    });
+
+    const { default: Conversations } = await import('../Conversations');
+
+    render(
+      <Provider store={store}>
+        <MemoryRouter>
+          <SidebarSlotProvider>
+            <SidebarSlotOutlet />
+            <Conversations />
+          </SidebarSlotProvider>
+        </MemoryRouter>
+      </Provider>
+    );
+
+    // The image marker's data URI still renders as an <img> (parsed out for display)...
+    await waitFor(() => {
+      const img = document.querySelector(`img[src="${dataUri}"]`);
+      expect(img).not.toBeNull();
+    });
+
+    // ...but the raw marker syntax must never leak into the rendered bubble text.
+    expect(document.body.textContent).not.toContain('[IMAGE:');
+    expect(document.body.textContent).not.toContain('[FILE:');
+    expect(document.body.textContent).toContain('read this');
+    expect(document.body.textContent).toContain('and');
+
+    // Copy-to-clipboard must use the same cleaned text as the bubble, not the
+    // raw msg.content with markers still embedded.
+    await act(async () => {
+      fireEvent.click(screen.getByTitle('Copy response'));
+    });
+    expect(writeText).toHaveBeenCalledWith('read this and');
+    expect(writeText).not.toHaveBeenCalledWith(expect.stringContaining('[IMAGE:'));
+    expect(writeText).not.toHaveBeenCalledWith(expect.stringContaining('[FILE:'));
+  });
 });
 
 describe('Conversations — thread rename', () => {