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Planning with Files

Manus-style persistent planning that keeps task_plan.md, findings.md and progress.md on disk so multi-step work survives /clear and auto-compaction.

AutomationIntermediate★ 26,060⑂ 2,177AI score 9/10Last updated: Aug 9, 2026

What it does

This skill treats the context window as RAM and the filesystem as disk. For any task that needs more than a few tool calls, it creates and continuously maintains three markdown files in your project directory:

  • task_plan.md — phases, status, next step, decision journal
  • findings.md — research and discoveries (especially fragile multimodal content from images, PDFs, browsers)
  • progress.md — session log, test results, errors encountered

It also registers hooks (UserPromptSubmit, PreToolUse, PostToolUse, Stop, PreCompact) that re-inject the plan each turn, and ships session-catchup.py to rebuild context after /clear. Extras include a 3-strike error protocol before escalating to you, isolated .planning/<date-slug>/ directories for parallel tasks, SHA-256 plan attestation, and opt-in autonomous / gated modes for long unattended runs.

Who it's for

  • Anyone handing Claude long refactors, builds, or research spanning many tool calls
  • Users frustrated by agents forgetting the goal or repeating the same failing action
  • Developers running several parallel tasks in one repo from different terminals
  • Teams that want a durable written record of what was tried and learned

Examples

  1. Large refactor: run init-session.sh "Backend Refactor", work phase by phase; when auto-compaction hits, the agent re-reads the plan files and resumes exactly where it stopped.
  2. Recovery after /clear: invoke the skill and it compares the catch-up report against git diff --stat, then writes the missing work back into the planning files.
  3. Long research task: the 2-action rule forces findings to disk after every two browse/view operations, so screenshot and PDF insights are never lost.

· · · Install guide · · ·

Install in the Claude app (no terminal)
  1. Download the ZIP with the button below.
  2. In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
  3. Go to Customize → Skills → + → 'Upload a skill' and upload the ZIP.
↓ Download ZIP
Install in Claude Code

Let Claude do it — paste this into Claude Code

Install the skill I found on Claude Skill Mart.
Copy the .pi/skills/planning-with-files folder from the GitHub repo OthmanAdi/planning-with-files into my ~/.claude/skills/pi-planning-with-files/.
When it's done, tell me in one line what this skill can do.

Install with a command instead

git clone https://github.com/OthmanAdi/planning-with-files.git ~/.claude/skills/planning-with-files

⚠ This is a third-party skill. Check the source repository before installing.

  1. Open a terminal and clone the skill: git clone https://github.com/OthmanAdi/planning-with-files.git ~/.claude/skills/planning-with-files
  2. If you also want the /plan-goal and /plan-loop slash commands, install it as a plugin from inside Claude Code: run /plugin marketplace add OthmanAdi/planning-with-files, then /plugin install.
  3. Verify the install with ls ~/.claude/skills/planning-with-files — you should see SKILL.md, scripts/ and templates/.
  4. Restart Claude Code so the hooks in the frontmatter are registered.
  5. Change into your project folder and ask something like "plan this out step by step"; the skill will create task_plan.md, findings.md and progress.md there.
  6. Optional: for parallel work run sh ~/.claude/skills/planning-with-files/scripts/init-session.sh "Task name", and run scripts/plan-doctor.sh if the hooks seem silent.
  7. Note: planning files land in your project root, so consider adding them to .gitignore, and start with the default (legacy) mode — gated mode can block session stop on supported hosts.
View source on GitHub ↗License: MIT