Session Watchdog

Monitors context levels, warns before compaction, and saves checkpoints to preserve important information.

Context Thresholds

Check Context

Before each session and periodically during long conversations:

session_status

Check the contextTokens field from the response.

Checkpoint Protocol

When approaching 80% (160k tokens):

1. Save checkpoint to memory file:

   • Read current memory/YYYY-MM-DD.md
   • Add key context: decisions, pending tasks, important details
   • Write back to memory file

2. Alert user: Say: "⚠️ Approaching context limit (~160k tokens). Saving checkpoint to memory before continuing."

3. Ask user:

   • Continue and accept compaction?
   • Summarize and restart fresh?
   • Pause until ready?

What to Save

Essential information that must survive compaction:

• Decisions made in this conversation
• Pending tasks not yet completed
• Important context (project state, configurations, preferences)
• Files modified and their paths
• Unresolved issues requiring follow-up

When to Trigger

• At session start
• After every 30k tokens of conversation
• Before initiating large tasks (file edits, multiple operations)
• When user asks "how much context do we have left?"

Memory File Format

# YYYY-MM-DD

## Session Checkpoint (at X% context)

### Decisions
- Decision 1
- Decision 2

### Pending
- [ ] Task 1
- [ ] Task 2

### Important Context
- Project state: ...
- Last file modified: ...

### Unresolved
- Issue needing follow-up