Session Continuity Improvements

Session Continuity Improvements

Priority: MEDIUM

Problem:
Multiple "Session resumed" messages in transcripts suggest dropped context or timeouts. When session resumes, context about what was in progress is lost.

Current Behavior:

Session drops without warning
When resumed, no summary of what was in progress
User must remind AI of context
Expected Behavior:

Before session timeout, save state summary
On resume, show: "Session resumed. We were working on [X]. Last status: [Y]. Should I continue with [Z]?"
Give user option to change direction if context shifted
Impact:

Lost work and context
User must re-explain situation
Inefficient restart after interruption