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 .gsd/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 .gsd/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 .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

• Write a state snapshot to .gsd/STATE.md immediately when a threshold is hit

• Include at minimum: current phase, current task, last action, next step

• 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