Built-in Learning Memory and Documentation Prompts

Built-in Learning Memory and Documentation Prompts

Priority: HIGH

Problem:
Claude Code doesn't persist learnings between sessions or even within a session. Despite explicit user request: "please write details to Claude.MD so we don't need to go through this discovery again" - this was never done. All learnings were lost.

Current Behavior:

Discoveries made during debugging are forgotten
No automatic documentation of solutions
Same issues will be debugged again in future sessions
CLAUDE.md files exist but aren't proactively updated
Expected Behavior:

When CLAUDE.md exists, periodically offer: "I discovered X. Should I document this in CLAUDE.md?"
After resolving a complex issue, automatically suggest documentation
At end of session, summarize learnings and offer to save them
Make documentation a first-class part of workflow
Impact:

Wasted effort re-discovering same solutions
No knowledge accumulation over time
CLAUDE.md becomes stale despite being valuable resource
Suggested Implementation:

Detect when CLAUDE.md exists in project
After significant discoveries, prompt: "Should I update CLAUDE.md with what we learned about [topic]?"
At end of complex debugging, offer session summary
Make it easy to say "yes, document that" without interrupting flow
Real Example:
User explicitly requested documentation in transcript line 51, but AI never updated CLAUDE.md despite 700+ more lines of work. All iOS credential learnings were lost.