context-health-monitor_skill

Overview

This skill monitors an agent's conversational context for signs of degradation and proactively saves state before quality drops. It detects repeated failures, circular behavior, and explicit uncertainty, then writes concise state dumps and recommends pausing or changing course. The goal is to preserve useful context and avoid wasted effort when sessions become unreliable.

How this skill works

The monitor observes agent signals like repeated debugging attempts, identical approaches tried twice, phrases that indicate confusion, and long back-and-forth sessions. When thresholds are reached it immediately writes a structured state snapshot to .gsd/STATE.md (and uncertainty notes to .gsd/DECISIONS.md) and then notifies the user with a recommendation to pause or try a new approach. It enforces a 3-strike stop rule, circular-detection flow, and explicit uncertainty logging.

When to use it

• During long interactive sessions where context may drift or accumulate noise
• When the same fix or debugging step has failed multiple times
• If the agent repeats approaches or cycles through the same logic
• When the agent expresses uncertainty or backtracking language
• Before recommending a session pause or handoff to preserve state

Best practices

• Always auto-save state immediately on hitting a warning threshold before prompting the user
• Record what was attempted, outcomes, current hypothesis, and recommended next steps in the state dump
• Acknowledge repetition and present a clearly different alternative rather than repeating the same steps
• Ask the user for guidance when uncertain instead of guessing
• Keep state files concise and machine-parseable to support automated resume

Example use cases

• A debugging loop hits the same error three times: the skill saves a state dump and recommends starting a fresh session
• The agent cycles between two strategies: the skill lists tried approaches and proposes a fundamentally different plan
• The agent says 'I'm not sure' about a migration step: the skill logs the uncertainty and requests user direction
• During an extended design conversation the skill recommends /pause and writes the current phase, last action, and next step to state
• Automated handoffs where /resume will reload the precise saved context for a new session