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:

•STOP attempting fixes
•
Document in .agent/state/STATE.md:
- •What was tried
- •What errors occurred
- •Current hypothesis
•Recommend user start fresh session
•Do NOT continue with more attempts

Rule 2: Circular Detection

If the same approach is being tried again:

•Acknowledge the repetition
•List what has already been tried
•Propose a fundamentally different approach
•Or recommend /pause for fresh perspective

Rule 3: Uncertainty Logging

When uncertain about an approach:

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

State Dump Format

When triggered, write to .agent/state/STATE.md:

markdown

## 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]

Integration

This skill integrates with:

•/pause — Triggers proper session handoff
•/resume — Loads the state dump context
•Rule 3 in GEMINI.md — Context Hygiene enforcement