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Planning with Files

Persists agent working memory on disk via task_plan.md, findings.md and progress.md so long multi-step tasks survive context compaction and session breaks.

AutomationIntermediate★ 27,953⑂ 2,313AI score 10/10Last updated: Nov 7, 2026

What it does

  • Before any complex task it initializes task_plan.md (phases + status), findings.md (research), and progress.md (session log) in your project directory — "working memory on disk."
  • Phases use a strict ### Phase N: Name + single **Status:** pending/in_progress/complete format, validated by check-complete.sh --validate.
  • Lifecycle hooks (UserPromptSubmit, PreToolUse, PostToolUse, Stop, PreCompact) re-inject the selected plan so state is recovered after compaction or a dropped session.
  • Enforces practical rules: the 2-action rule (write findings after every two view/search ops), the 3-strike error protocol (diagnose → alternative → rethink → escalate), and an error log table.
  • set-active-plan.sh --list shows saved plans and phase progress; archiving happens only with explicit user approval.

Who it's for

  • Anyone delegating work that needs 5+ tool calls: research, refactors, feature builds.
  • Users whose agent drifts from the goal or repeats the same failed fix in long sessions.
  • Teams running multi-session or parallel tasks that need separately pinned plans.

Example uses

  1. Multi-session feature work: initialize a "refactor payments module" plan with Phases 1–5; next day the hooks restore the current phase and findings automatically.
  2. Competitor research: after every two pages read, key numbers go into findings.md so multimodal/browser data is captured before it falls out of context.
  3. Hard bug hunt: each attempt and error message is logged to the ## Errors Encountered table, preventing repeats and triggering a clear escalation after three failures.

· · · 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 AI 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. Open a terminal and clone the repo: git clone https://github.com/OthmanAdi/planning-with-files.git /tmp/pwf
  2. Copy the skill into your user skills path: mkdir -p ~/.claude/skills && cp -r /tmp/pwf/.cursor/skills/planning-with-files ~/.claude/skills/
  3. Make the helpers executable: chmod +x ~/.claude/skills/planning-with-files/scripts/*.sh
  4. Confirm Python exists (needed by the catch-up script): python3 --version
  5. If you installed to a non-standard path, add export PWF_SCRIPT_DIR=~/.claude/skills/planning-with-files/scripts to your shell profile so the hooks can find the script.
  6. Restart Claude Code, then from your project root ask it to "create a plan for this task" — planning files appear under .planning/.
  7. On Windows, use the PowerShell variants: init-session.ps1, check-complete.ps1, set-active-plan.ps1.
View source on GitHub ↗License: MIT