[Bug] Auto-compact context summarization loses critical instructions and workarounds

Bug Description
Too many critical instructions are being lost during auto context compact and summarization.

Claude has trouble accurately identifying critical information in a complex session and keeping it.

Especially prominent:

A) If during a session, an issue with using a helper script for Claude occurs, the summarization does not keep the solution or workaround. Instead, it falls back to its default behaviour.

B) If the previous full context included information about specific script usage and bash/pwsh shell CLI usage, that information is lost after summarization.

Result: This makes it very tedious to work in a long session without having to permanently update instruction memory files and have Claude re-ingest them via user intervention. This is also error prone during long autonomous task execution, that exceeds the context window length.

Environment Info

• Platform: win32
• Terminal: windows-terminal
• Version: 2.0.25
• Feedback ID: 1bc8f064-a42b-42a9-821a-498745d46168