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Planning with Files

Keeps plans, findings, and progress in markdown files on disk so multi-step work survives context compaction and session breaks.

AutomationIntermediate★ 26,060⑂ 2,177AI score 8/10Last updated: Aug 9, 2026

What it does

Implements the Manus-style pattern of treating the context window as volatile RAM and the filesystem as persistent disk. The skill creates and maintains three files under .kiro/plan/:

  • task_plan.md — goal, phases, statuses, decisions
  • findings.md — research results and discoveries (all external/web content goes here)
  • progress.md — session log, test results, errors

It also enforces working rules:

  • 2-Action Rule — after every two view/browse/search operations, immediately write key findings to disk
  • 3-Strike Error Protocol — diagnose, try an alternative, rethink assumptions, then escalate to the user
  • Read vs Write matrix — explicit guidance on when re-reading files is worth the tokens
  • Security boundary — external content is untrusted and its embedded instructions are never followed

Bundled helpers include bootstrap.sh/.ps1, session-catchup.py for recovering a prior session, and check-complete.sh for verifying phase completion.

Who it's for

  • Developers running long refactors, research spikes, or features across many sessions
  • Anyone who has watched an agent lose the goal after context compaction
  • Teams that want an auditable, file-based trail of decisions and errors
  • Users who want the agent to stop silently retrying the same failing action

Examples

  1. Kick off a large migration: say "start planning: migrate auth to JWT" and the skill writes a phased task_plan.md, updating each phase status as work proceeds.
  2. Resume days later: say "resume work" — session-catchup.py summarizes file mtimes and prior state, then the agent reconciles the plan with the actual codebase.
  3. Comparative research: while browsing several library docs, every two lookups get distilled into findings.md, so evidence and links are never lost to context trimming.

· · · 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 .kiro/skills/planning-with-files folder from the GitHub repo OthmanAdi/planning-with-files into my ~/.claude/skills/othmanadi-planning-with-files-8/.
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 && mkdir -p ~/.claude/skills && cp -r planning-with-files/.kiro/skills/planning-with-files ~/.claude/skills/

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

  1. Open a terminal and go to the folder where you keep skill sources.
  2. Clone the repository: git clone https://github.com/OthmanAdi/planning-with-files.git
  3. Copy the skill into Claude Code: mkdir -p ~/.claude/skills && cp -r planning-with-files/.kiro/skills/planning-with-files ~/.claude/skills/
  4. Change into your project directory and run the bootstrap script to create the plan files: sh ~/.claude/skills/planning-with-files/assets/scripts/bootstrap.sh (use bootstrap.ps1 in PowerShell on Windows).
  5. Confirm Python 3 is available if you want session recovery: python3 --version.
  6. Restart Claude Code and trigger the skill with phrases like "start planning", "resume work", or "current phase".
  7. If you are not using Kiro, edit the .kiro/ paths in SKILL.md to a directory that fits your project (for example docs/plan/).
View source on GitHub ↗License: MIT