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name: session-watchdog description: Monitor session context levels and proactively save checkpoints before compaction. Use when: (1) session context exceeds 80% capacity, (2) user asks about session status or memory, (3) at the start of each new session to check context, or (4) before long tasks that might push context over threshold.

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