SendUserFile (Cowork) returns HTTP 429 continuously for 23h+, blocking file delivery — not a Drive/usage quota issue

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Plan: Team (Bons Vivants organization)

Context: Cowork session, transferring ~1556 files from the cloud workspace to Google Drive via the "device bridge" to a Windows PC. File transfer goes through the internal SendUserFile tool.

Problem: After successfully delivering 262 files, every subsequent call to SendUserFile fails with upload failed: server returned 429, including on a freshly created few-byte test text file.

Duration: Continuous block since 20:59 UTC on 2026-08-14, still active as of 20:48 UTC on 2026-08-15 — more than 23h45, across 20+ spaced attempts (15-45 min, then 1-2h intervals).

Causes ruled out with direct evidence:

Google Drive quota (checked official Google docs; manual Drive access still works fine in parallel)
Cowork/Claude usage limit (Settings > Usage checked twice, 13h apart: 50% then 1% of session used)
Device bridge / PC issue (bridge re-verified healthy, folder reads succeed)
Parallel transfers (already strictly sequential, one file at a time)

Note: This is unrelated to another open support ticket about being unable to enable the native Google Drive connector for this organization — please do not merge them.

Impact: Delivery of accounting documents (annual closing statements) blocked; a full working day lost.

What Should Happen?

SendUserFile should successfully deliver files without returning a persistent HTTP 429 rate-limit error — especially since Google Drive quota and Cowork usage-limit causes have both been ruled out with direct evidence.

Error Messages/Logs

upload failed: server returned 429

Continuous since 20:59 UTC on 2026-08-14, still failing as of 20:51 UTC on 2026-08-15 (>23h50), across 25+ spaced test attempts (a fresh few-byte test file each time).

Steps to Reproduce

1. Open a Cowork session and perform a file-delivery/transfer task using SendUserFile (e.g. delivering files gathered via the device bridge to a connected local machine).
2. Successfully deliver a batch of files (in this case, 262 out of 1556).
3. Continue calling SendUserFile for subsequent files (or even a freshly created few-byte test text file).
4. Every call fails with: "upload failed: server returned 429".
5. Wait and retry at increasing intervals (15-45 min, then 1-2h) over 23h50+ — the error persists identically every time, including on trivial isolated test files unrelated to the original batch.

Note: this is not caused by file size/name/content (fails even on a tiny test file), not a Google Drive quota (Drive works fine via manual access in parallel, and official Drive quotas don't match this duration), not a Cowork/Claude usage limit (Settings > Usage checked twice, 13h apart: 50% then 1%), and not a device-bridge/PC issue (bridge re-verified healthy throughout).

Claude Model

Sonnet (default)

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

N/A — using Cowork (desktop app), not the Claude Code CLI

Platform

Other

Operating System

Windows

Terminal/Shell

Other

Additional Information

Note: filing here for lack of a more specific venue — the actual affected product is Cowork (cloud-hosted, accessed via the Claude desktop app), not the Claude Code CLI. The version/OS/terminal fields above don't strictly apply since Cowork runs in Anthropic's hosted cloud sandbox rather than a local CLI install.