diff --git a/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx b/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx
index 4b27ae1423..e6525ff8c4 100644
--- a/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx
+++ b/client/src/components/Chat/Messages/Content/Parts/Attachment.tsx
@@ -589,14 +589,18 @@ export function AttachmentGroup({ attachments }: { attachments?: TAttachment[] }
   mermaidArtifacts.sort(bySalience);
   imageAttachments.sort(bySalience);
 
+  const downloadableFileAttachments = fileAttachments.filter((attachment) =>
+    Boolean(attachment.filepath),
+  );
   const downloadableTextAttachments = textAttachments.filter((attachment) =>
     Boolean(attachment.filepath),
   );
   const textOnlyAttachments = textAttachments.filter((attachment) => !attachment.filepath);
-  const groupDownloadableFiles = fileAttachments.length + downloadableTextAttachments.length > 1;
+  const groupDownloadableFiles =
+    downloadableFileAttachments.length + downloadableTextAttachments.length > 1;
   const groupedFileAttachments = groupDownloadableFiles
-    ? [...fileAttachments, ...downloadableTextAttachments].sort(bySalience)
-    : fileAttachments;
+    ? [...downloadableFileAttachments, ...downloadableTextAttachments].sort(bySalience)
+    : downloadableFileAttachments;
   const visibleTextAttachments = groupDownloadableFiles ? textOnlyAttachments : textAttachments;
 
   return (
diff --git a/client/src/components/Chat/Messages/Content/Parts/__tests__/TextAttachment.test.tsx b/client/src/components/Chat/Messages/Content/Parts/__tests__/TextAttachment.test.tsx
index c0155fdafc..b7275ee560 100644
--- a/client/src/components/Chat/Messages/Content/Parts/__tests__/TextAttachment.test.tsx
+++ b/client/src/components/Chat/Messages/Content/Parts/__tests__/TextAttachment.test.tsx
@@ -198,4 +198,28 @@ describe('AttachmentGroup', () => {
     expect(container.querySelector('pre')).toBeNull();
     expect(screen.getAllByTestId('file-container').length).toBeGreaterThan(0);
   });
+
+  it('does not collapse a single downloadable text preview with a non-downloadable placeholder', () => {
+    const attachments = [
+      textAttachment({
+        file_id: 'placeholder',
+        filename: 'placeholder.zip',
+        filepath: '',
+        type: 'application/zip',
+        text: undefined as unknown as string,
+      }),
+      textAttachment({
+        file_id: 'json',
+        filename: 'output.json',
+        filepath: '/files/output.json',
+        text: '{"ok":true}',
+      }),
+    ] as TAttachment[];
+
+    const { container } = render(<AttachmentGroup attachments={attachments} />);
+
+    expect(screen.queryByRole('button', { name: 'com_ui_show_n_files' })).not.toBeInTheDocument();
+    expect(container.querySelector('pre')?.textContent).toBe('{"ok":true}');
+    expect(screen.getByTestId('file-container')).toHaveTextContent('output.json');
+  });
 });