Cloud agent cannot retrieve certain uploaded file types (PDF, CSV)

Where does the bug appear (feature/product)?

Cloud Agent (GitHub, Slack, Web, Linear)

Describe the Bug

When I upload certain file types such as a PDF or CSV to a Cloud Agent, the agent responds with:

The uploaded file Invoice-XBBU8UZ0-0010 (2).pdf did not reach the VM. The expected path /home/ubuntu/.cursor/projects/workspace/uploads/ does not exist, and a filesystem-wide search for the filename or any recent PDF returns nothing.

When I upload a PNG, the agent can retrieve it.

Steps to Reproduce

Upload a PDF or CSV to a Cloud Agent.

Expected Behavior

The agent should be able to access a PDF or CSV.

Operating System

MacOS

Version Information

Version: 3.20.21
VS Code Extension API: 1.128.0
Commit: f09fca384ceca23f7bf21f9c23655b162641d740
Date: 2026-09-13T19:02:51.781Z
Layout: Agent Window
Build Type: Stable
Release Track: Default
Electron: 42.10.0
Chromium: 148.0.7778.280
Node.js: 24.18.1
V8: 14.8.178.38-electron.0
xterm.js: 6.1.0-beta.291
OS: Darwin arm64 25.6.0

For AI issues: add Request ID with privacy disabled

Request ID: 5d46d8f2-8210-430c-a7ac-c800af929168

Does this stop you from using Cursor

Sometimes - I can sometimes use Cursor

Hey @Lewis_Blackwood!

Thanks for reporting this.

I’m having trouble reproducing this. Can you share how you’re attaching the files to the cloud agent? Are you you going through + > Files > xyz.pdf or doing a drag/drop or copy/paste? Does the behavior change depending on which you do?

It doesn’t work either way. Initial report was via drag and drop. Here’s a request ID using ‘+ Files’ (same issue): e536b21d-b45e-42e6-b5b9-c9b0a7ada63e

I noticed this first around a week ago with CSV files and reported it via the Cursor shared Slack for our YC batch.

No. The file did not arrive on this VM.

  1. Expected path /home/ubuntu/.cursor/projects/workspace/uploads/Invoice-XBBU8UZ0-0010__2__b0a4.pdf does not exist; the uploads/ directory was never created.
  2. A filesystem-wide search for *XBBU8UZ0* (retried after 15 s) returns nothing.

Cause: the upload attachment was registered in the message but the file transfer to the VM failed or was skipped.

Next action (under 2 minutes): re-attach the PDF in a new message and I will read it immediately.

Hey @Lewis_Blackwood, thanks for trying both ways, that ruled a lot out.

I think I know what is going on, and it looks specific to your repo. The agent saves attached PDFs and CSVs into its uploads folder using the same file-write step that the agent’s own Write tool uses. If the repo has a Cursor hook that denies the Write tool (for example a rule that blocks edits while on main), that hook also blocks the attachment from being saved, and right now the agent is not told about it, so it goes looking for a file that was never written. Images are handed to the model directly, which is why PNGs still work.

Could you check whether your repo has a .cursor/hooks.json with a preToolUse hook that matches Write? If it does, a quick workaround is to let that hook allow any file_path under /home/ubuntu/.cursor/projects/ (that is where attachments land) and only deny paths inside your repo. After that change, a new Cloud Agent with a PDF attached should be able to read it right away.

Let me know if the hook is there and whether the tweak fixes it for you.

Yes, you’re right! Looks like it was blocked by a hook. Sorted on my side - thanks!