[BUG] Repeated "image could not be processed" errors consumed ~60% of usage limit — 19 consecutive failures, each resending full 34MB context

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?

An image pasted into a long-running session (transcript ~33.9MB) began failing with "an image in the conversation could not be processed and was removed". The client retried 19 times in 14 minutes (02:26–02:40 UTC, 2026-06-10), and each failed attempt resent the full conversation context. This error loop alone consumed roughly 60% of my 5-hour usage window before I hit the limit. A fresh session then lost a further ~6% to the same error after pasting another screenshot. The error storm immediately preceded the "Elevated Errors on Claude Opus 4.8 (Fast Mode)" incident (02:50–03:30 UTC) on status.claude.com.

What Should Happen?

When an image fails processing, it should be dropped or replaced after the first failure — not retried 19 times with the full context resent and counted against the user's usage limit on every attempt.

Error Messages/Logs

API Error: an image in the conversation could not be processed and was removed. Re-read the file with a different approach if you still need it.

Session 88a4547e-c623-4ace-a260-2eec3c47a30f — 2026-06-10 UTC:
02:26:45, 02:27:08, 02:27:29, 02:27:50, 02:28:03, 02:28:16, 02:28:39,
02:29:54, 02:30:38, 02:32:11, 02:33:41, 02:34:36, 02:38:07, 02:39:07,
02:39:37, 02:39:44, 02:40:18, 02:40:32, 02:40:44 (19 occurrences)
plus 2 more at 04:31:04 and 04:31:34

Session b9d142b2-ca17-459c-8e56-37309c7b47ca — 2026-06-10 UTC:
04:32:36 (fresh session, same error after pasting a screenshot)

Steps to Reproduce

1. Use Claude Code (VSCode extension) in a long-running session — transcript file ~33.9MB.
2. Paste a screenshot image into the conversation.
3. The image fails processing with the error above; the client keeps retrying (19 times in 14 minutes), resending the full conversation context each time.
4. Usage limit drains rapidly until the session limit is hit.

Note: reproduced in a brand-new session (b9d142b2...) by pasting another screenshot — lost ~6% there too.

Claude Model

Opus

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.1.170 (VSCode extension, win32-x64)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

VS Code integrated terminal

Additional Information

• Models used in the affected session: claude-opus-4-8 (1,669 messages) and claude-fable-5 (294 messages) — errors occurred on both.
• Environment: Claude Code VSCode extension 2.1.170 (win32-x64), Windows 10 Pro 10.0.19045.
• Anthropic support (Fin AI agent) reviewed this case, confirmed the timing matches the Opus 4.8 Fast Mode incident, and advised filing a GitHub issue with session IDs, exact timestamps, and error messages so the team can verify server logs and consider a goodwill token restoration.
• Happy to provide the local session transcripts if useful.

<img width="1294" height="761" alt="Image" src="https://github.com/user-attachments/assets/c818f663-8e27-4c86-958f-0863348f4a70" />
<img width="1656" height="646" alt="Image" src="https://github.com/user-attachments/assets/cfca9f64-396c-4ba8-a989-1c1c57a7384b" />
<img width="964" height="268" alt="Image" src="https://github.com/user-attachments/assets/7eaf8cc0-9e75-47be-aa23-b20ef2ab3fa5" />