Meta-cognitive decision support that analyzes current context and surfaces intelligent next-step options to the user. Use this skill when: (1) User explicitly invokes /checkpoint, (2) Significant work has been completed and a checkpoint is valuable, (3) Uncertainty or ambiguity exists about requirements or approach, (4) Task complexity has expanded beyond initial scope, (5) Before finalizing or committing to ensure nothing is missed. This skill pauses execution, assesses the situation holistically, and presents 2-5 contextually-appropriate options via AskUserQuestion, with a recommended option and rationale.
View on GitHubskills/checkpoint/SKILL.md
February 5, 2026
Select agents to install to:
npx add-skill https://github.com/petekp/agent-skills/blob/main/skills/checkpoint/SKILL.md -a claude-code --skill checkpointInstallation paths:
.claude/skills/checkpoint/# Checkpoint Pause, assess, and surface intelligent next-step options to the user. ## When to Trigger Proactively Suggest this skill (without being asked) when detecting: - **Completion signal**: A feature, fix, or milestone just finished - **Uncertainty signal**: Requirements unclear, multiple valid paths, or low confidence in current direction - **Complexity signal**: Scope expanded, unexpected dependencies emerged, or task is taking longer than expected - **Drift signal**: Work may have diverged from user's original intent - **Quality signal**: Code works but may benefit from review, testing, or refactoring ## Workflow ### 1. Context Assessment Silently evaluate the current state across these dimensions (do not output this analysis): - **Progress**: What has been accomplished? What remains? - **Quality**: Is the work solid, or are there rough edges? - **Alignment**: Does recent work match what the user actually wants? - **Uncertainty**: What assumptions were made? What's unclear? - **Risk**: What could go wrong? What hasn't been tested? - **Efficiency**: Is there a better path forward? ### 2. Generate Options Based on assessment, generate 2-5 contextually-appropriate options. Draw from (but don't limit to) these archetypes: | Archetype | When Relevant | |-----------|---------------| | **Commit progress** | Meaningful progress made, good stopping point | | **Systems audit** | Complex changes, potential for bugs or regressions | | **Prioritize/plan** | Multiple pending tasks, unclear what matters most | | **Re-evaluate decisions** | Low confidence in recent choices, new information available | | **Clarify with user** | Assumptions made, requirements ambiguous | | **Test/verify** | Code works but edge cases untested | | **Refactor/clean up** | Code functional but messy | | **Document** | Complex logic that needs explanation | | **Step back** | May be overcomplicating or missing simpler solution | | **Continue current path** | Clear next step, no reason to