Session Management

Prevents context loss in long coding sessions by maintaining tiered checkpoints. Quick updates after small tasks, full checkpoints after decisions or 20 tool calls, and session archives when wrapping up major work. Creates a session directory with current state, decision logs, and code landmarks so you can resume exactly where you left off. The tiered approach is smart: it won't bog you down with documentation after every tiny change, but it forces you to document the stuff that actually matters, like why you chose RS256 over HS256 or where the auth middleware lives. Most useful when you're deep in a multi-day feature and need to preserve architectural context across breaks.

skills.sh installs: 201
GitHub stars: 685
last updated: Jun 3, 2026

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Install

$ npx -y skills add alinaqi/claude-bootstrap --skill session-management --agent claude-code

Installs into .claude/skills of the current project.

Files

Session Management Skill

For maintaining context across long development sessions and enabling seamless resume after breaks.

Core Principle

Checkpoint at natural breakpoints, resume instantly.

Long development sessions risk context loss. Proactively document state, decisions, and progress so any session can resume exactly where it left off - whether returning after a break or hitting context limits.

Tiered Summarization Rules

Tier 1: Quick Update (current-state.md only)

Trigger: After completing any small task or todo item Action: Update "Active Task", "Progress", and "Next Steps" sections Time: ~30 seconds