Auto-compact fails when context exceeds 100 images/documents limit

[mpale80]

Bug Description

When a conversation accumulates more than 100 images/documents, both regular API calls and /compact fail with:

API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"too many images and documents: 101 + 0 > 100"}}

Problem

• Auto-compact is enabled but doesn't trigger before reaching the 100 image/document limit
• Once the limit is exceeded, /compact also fails (it needs to send context to API to create summary)
• The only recovery is /clear, losing all conversation context

Expected Behavior

Auto-compact should trigger proactively when approaching the image/document limit (e.g., at 80-90 images), not just based on token count.

Environment

• Claude Code version: 2.1.44
• Installation: Native (/usr/bin/claude)
• Platform: Linux (Debian)

Suggested Fix

Add image/document count check to auto-compact trigger logic, in addition to token-based triggers.

[github-actions]

Found 1 possible duplicate issue:

1. [BUG] Failure when there's over 100 images #19822

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[github-actions]

This issue has been automatically locked since it was closed and has not had any activity for 7 days. If you're experiencing a similar issue, please file a new issue and reference this one if it's relevant.