Context Health Monitor

Purpose

Prevent "Context Rot" — the quality degradation that occurs as the agent processes more information in a single session.

When This Skill Activates

The agent should self-monitor for these warning signs:

Warning Signs

Signal	Threshold	Action
Repeated debugging	3+ failed attempts	Trigger state dump
Going in circles	Same approach tried twice	Stop and reassess
Confusion indicators	"I'm not sure", backtracking	Document uncertainty
Session length	Extended back-and-forth	Recommend /pause

Behavior Rules

Rule 1: The 3-Strike Rule

If debugging the same issue fails 3 times:

1. STOP attempting fixes
2. Document in .gsd/STATE.md:
   • What was tried
   • What errors occurred
   • Current hypothesis
3. Recommend user start fresh session
4. Do NOT continue with more attempts

Rule 2: Circular Detection

If the same approach is being tried again:

1. Acknowledge the repetition
2. List what has already been tried
3. Propose a fundamentally different approach
4. Or recommend /pause for fresh perspective

Rule 3: Uncertainty Logging

When uncertain about an approach:

1. State the uncertainty clearly
2. Document in .gsd/DECISIONS.md:
   • The uncertain decision
   • Why it's uncertain
   • Alternatives considered
3. Ask user for guidance rather than guessing

State Dump Format

When triggered, write to .gsd/STATE.md:

## Context Health: State Dump

**Triggered**: [date/time]
**Reason**: [3 failures / circular / uncertainty]

### What Was Attempted
1. [Approach 1] — Result: [outcome]
2. [Approach 2] — Result: [outcome]
3. [Approach 3] — Result: [outcome]

### Current Hypothesis
[Best guess at root cause]

### Recommended Next Steps
1. [Fresh perspective action]
2. [Alternative approach to try]

### Files Involved
- [file1.ext] — [what state it's in]
- [file2.ext] — [what state it's in]

Auto-Save Protocol

Critical: When any warning signal triggers, the agent must save state BEFORE recommending /pause to the user. This ensures state persists even if the session hard-terminates.

Steps

1. Write a state snapshot to .gsd/STATE.md immediately when a threshold is hit
2. Include at minimum: current phase, current task, last action, next step
3. Then inform the user of the situation and recommend /pause

Why

Sessions can terminate abruptly (usage limits, context limits, network errors). If the agent waits for the user to type /pause, it may never get the chance. By saving first and recommending second, state is always preserved.

Integration

This skill integrates with:

• /pause — Triggers proper session handoff (includes proactive auto-save)
• /resume — Loads the state dump context
• Rule 3 in GEMINI.md — Context Hygiene enforcement