[BUG] Context overflow causes loss of work - no automatic persistence

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?

• 2.5 hours of audit work lost due to context overflow between sessions
• Claude was instructed to write results to file after each session but failed to do so
• Summarization on context limit doesn't preserve detailed findings
• Need: auto-save mechanism or forced file write before context overflow

What Should Happen?

Expected Behavior

• Claude should AUTO-SAVE work progress to a file BEFORE context overflow/summarization
• Or at minimum: warn user "Context nearly full, saving progress to file now"
• When explicitly asked to save to file, Claude MUST verify the write succeeded

Actual Behavior

• Claude agrees to save but doesn't execute the file write
• Summarization loses all granular details (specific bugs, line numbers, etc.)
• 2.5 hours of detailed audit work reduced to vague summary

Impact

• Lost: 2.5 hours of work + tokens consumed
• No way to recover detailed findings
• User must redo entire audit from scratch

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

Claude Code v2.1.5

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Cursor

Additional Information

_No response_