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Planning with Files

Gives Claude persistent on-disk working memory — task_plan.md, findings.md, progress.md — so long multi-step work survives context loss and compaction.

AutomationIntermediate★ 27,074⑂ 2,254AI score 10/10Last updated: Sep 22, 2026

What it does

  • Creates and maintains task_plan.md (phases, decisions), findings.md (research), and progress.md (session log) inside your project directory.
  • Enforces the "context = RAM, filesystem = disk" pattern: anything important gets written out before it's lost.
  • Registers lifecycle hooks (UserPromptSubmit, PreToolUse, PostToolUse, Stop, PreCompact) that inject the selected plan context and preserve state across compaction.
  • Ships helper scripts: init-session.sh, check-complete.sh, set-active-plan.sh --list, and session-catchup.py --metadata/--replay for same-project session aggregation.
  • Encodes operating rules: save findings every 2 view/search operations, re-read the plan before decisions, log every error, and escalate after 3 failed attempts.

Who it's for

  • Anyone running research, refactors, or build-outs that span 5+ tool calls.
  • Users frustrated by an agent that forgets the goal mid-session or repeats the same failing action.
  • Teams running parallel tasks who need each plan pinned via PLAN_ID or separate worktrees.

Example uses

  1. "Audit the auth flow across this repo" → init-session.sh "auth-audit" creates the plan dir; discoveries land in findings.md every couple of lookups.
  2. A long migration hits context compaction — the PreCompact hook plus re-reading task_plan.md restores exactly which phase is in progress.
  3. A build keeps failing — the 3-strike protocol forces a different approach and records each attempt in the error table so nothing is retried blindly.

· · · Install guide · · ·

Try it now, no install

Paste this into Claude to use the skill without installing anything.

Read the instructions in this file and follow them to help me:
https://raw.githubusercontent.com/OthmanAdi/planning-with-files/HEAD/.cursor/skills/planning-with-files/SKILL.md

What I want: (describe your task here)

If Claude can't open the link, open it yourself and paste the contents instead.

↓ If it works for you, download the ZIP below and install it. Then it runs on its own — no pasting each time.

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 .cursor/skills/planning-with-files folder from the GitHub repo OthmanAdi/planning-with-files into my ~/.claude/skills/othmanadi-planning-with-files-4/.
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 /tmp/pwf && mkdir -p ~/.claude/skills && cp -r /tmp/pwf/.cursor/skills/planning-with-files ~/.claude/skills/

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

  1. Clone the repo: git clone https://github.com/OthmanAdi/planning-with-files.git /tmp/pwf
  2. Create the skills folder: mkdir -p ~/.claude/skills
  3. Copy the skill in: cp -r /tmp/pwf/.cursor/skills/planning-with-files ~/.claude/skills/
  4. Make scripts executable: chmod +x ~/.claude/skills/planning-with-files/scripts/*.sh
  5. Confirm Python is available (python3 --version) for session-catchup.py.
  6. If you installed to a non-standard path, export the override: export PWF_SCRIPT_DIR=~/.claude/skills/planning-with-files/scripts
  7. Restart Claude Code, open your project root, and ask it to "create a plan file for this task" — verify task_plan.md appears in the project, not the skill folder.
  8. Sanity-check the listing command: sh ~/.claude/skills/planning-with-files/scripts/set-active-plan.sh --list
View source on GitHub ↗License: MIT