I got tired of re-explaining my codebase to every AI tool - so I built Checkpoint

B Kalyan Kumar — Tue, 02 Jun 2026 15:49:03 +0000

Every time I switched between Claude, Codex, and Claude Code, I spent the first few minutes of the session re-explaining the same things — what I was building, what the current task was, what decisions had already been made.

The tools don't share memory with each other. I was the context bus.

So I built Checkpoint — a local CLI that gives your repo a continuity layer. (The project's called contextos; checkpoint is the command you actually type.) It writes readable Markdown files to .contextos/ and generates a focused continuation pack for the next AI tool:

checkpoint continue --from codex --for claude-code

The output is a compact Markdown handoff: current task, relevant decisions, files to inspect, next action. You paste it or pipe it to the next agent.

Here's what a pack actually looks like (example — replace with your real output):

# Continuation Pack — for Claude Code
Generated from: codex · 2026-06-02

## Current task
Wire secret redaction into `checkpoint continue` before the pack is printed.

## Decisions that matter here
- Redaction runs on the assembled pack, not per-file (one pass, fewer misses).
- Patterns live in .contextos/context/constraints.md so they're reviewable.

## Files to inspect
- src/checkpoint/redact.py  — regex set + entropy check
- src/checkpoint/render.py  — where the pack is assembled

## Next action
Add a failing test for an AWS key in a task note, then make it pass.

Install

pip install checkpoint-cli

Or with uv:

uv tool install checkpoint-cli

Get started in 60 seconds

checkpoint setup-user   # one-time user preferences
checkpoint init         # adds .contextos/ to your project
checkpoint status       # check what memory exists
checkpoint continue     # generate the continuation pack

How it works

Everything lives in plain Markdown files you can read, edit, diff, and commit:

.contextos/
  context/        # architecture, constraints, decisions
  tasks/          # active and completed work
  handoffs/       # latest.md always has the most recent state
  state/          # local event log

checkpoint continue reads those files, applies secret redaction, and prints a pack shaped for the target agent — Codex, Claude, Claude Code, Cursor, Aider, or generic.

No account. No cloud. No hidden state. Apache-2.0.

Why local-first matters

You decide what context moves to the next tool. The files are yours - readable before they're sent anywhere, and secrets get redacted on the way out.

Where it is now