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Planning with Files

Keeps task_plan.md, findings.md and progress.md on disk so an AI agent never loses its goal or progress across long, multi-step work.

AutomationIntermediate27,0742,254AI score 10/10Last updated: Sep 22, 2026

What it does

  • Applies the "context window = RAM, filesystem = disk" pattern: anything important is written to a file.
  • Maintains three files — task_plan.md (phases, decisions), findings.md (research), progress.md (session log).
  • Lifecycle hooks (UserPromptSubmit, PreToolUse, PostToolUse, Stop, PreCompact) re-inject the selected plan into context each turn, wrapped in BEGIN/END data delimiters.
  • Enforces concrete rules: the 2-action save rule, a 3-strike error protocol, an error log table, and "never repeat a failing action".
  • Supports parallel tasks via .planning/<id>/ plus PLAN_ID/PWF_PLAN_ROOT pinning, optional SHA-256 plan attestation, and an opt-in completion gate with runaway guards.

Who it's for

  • Anyone running research, refactors or builds that need 5+ tool calls.
  • Users who keep losing state after context compaction or a dropped session.
  • Developers running several agent sessions against the same repository.

Examples

  1. Before a big refactor, run scripts/init-session.sh "Backend Refactor" and flip each phase to complete as you go.
  2. During web/PDF research, dump key findings into findings.md after every two view operations so multimodal detail isn't lost.
  3. Pin two terminals to different PLAN_IDs to run an incident investigation and a feature build side by side without clobbering each other's plan.

· · · 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/.agents/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 .agents/skills/planning-with-files folder from the GitHub repo OthmanAdi/planning-with-files into my ~/.claude/skills/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 /tmp/pwf && mkdir -p ~/.claude/skills && cp -r /tmp/pwf/.agents/skills/planning-with-files ~/.claude/skills/ && rm -rf /tmp/pwf

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

  1. Open a terminal and clone the repo: git clone https://github.com/OthmanAdi/planning-with-files.git
  2. Copy the skill folder into place: mkdir -p ~/.claude/skills && cp -r planning-with-files/.agents/skills/planning-with-files ~/.claude/skills/
  3. For the /plan-goal and /plan-loop slash commands, install via the plugin route instead: in Claude Code run /plugin marketplace add OthmanAdi/planning-with-files then /plugin install.
  4. Restart Claude Code, cd to your project root, and run sh ~/.claude/skills/planning-with-files/scripts/plan-doctor.sh to verify hooks and plan resolution.
  5. Start your first task with sh ~/.claude/skills/planning-with-files/scripts/init-session.sh "Task Name" and export PLAN_ID=<printed id> if you run parallel sessions.
  6. Stay in the default (legacy) mode at first; enable --autonomous or --gated only once you understand the Stop gate.