context-checkpoint

name	context-checkpoint
description	Save progress to a markdown file when context grows large or after many tool calls, preserving key decisions and state for continuity.
risk	safe
source	self
tags	["context","checkpoint","persistence"]

Context Checkpoint

When to Use

Trigger this skill when:

• Context window usage exceeds ~70% (conversation feels long, >30 tool calls)
• You notice repeated information or context drift
• Before a complex multi-step operation that may fill remaining context
• User explicitly asks to "save progress" or "checkpoint"

Instructions

1. Create checkpoint file at plans/checkpoint-{date}.md with this structure:

# Checkpoint — {brief task description}
Date: {ISO date}

## Current Task
{What we're doing and why}

## Completed
{Numbered list of completed steps with outcomes}

## In Progress
{Current step, what's been tried, current state}

## Key Decisions
{Important decisions made and their rationale}

## Key Files Modified
{File paths with brief description of changes}

## Remaining Work
{What still needs to be done}

## Context for Next Session
{Anything critical the next context window needs to know}

2. After creating checkpoint, inform the user: "Progress saved to plans/checkpoint-{date}.md. If context gets condensed, key state is preserved."

3. When resuming from checkpoint, read the latest checkpoint file first before continuing work.

Important

• Keep checkpoints CONCISE — bullet points, not paragraphs
• Include file paths and line numbers for modified code
• Capture the WHY behind decisions, not just the WHAT
• One checkpoint per task, overwrite if updating