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Planning with Files

File-based AI planning methodology using three persistent markdown files as working memory — includes 2-Action Rule, error recovery protocols, and session continuity across 16+ platforms.

development

Planning with Files

A structured AI planning methodology that solves the context loss problem by using three persistent markdown files as external memory. Version 2.23.0. Compatible with Claude Code, Cursor, Gemini CLI, GitHub Copilot, and 12+ other platforms.

Claims a 96.7% task success rate versus 6.7% without it. The core insight: AI agents lose track of complex tasks because they have no persistent working memory. Files fix that.

The Three Files

Working Memory System

  • task_plan.md — The master plan. What needs to be done, broken into steps, with current status
  • findings.md — Discoveries made during execution. Errors encountered, solutions found, decisions made
  • progress.md — Live progress log. What was done, what's next, session recovery checkpoint

These files persist across sessions. When a new session starts, the AI reads them to resume exactly where the previous session ended — no context rehashing required.

Core Protocols

2-Action Rule

The AI may only take 2 consecutive actions before writing back to the progress file. This prevents runaway execution and keeps the human in the loop at predictable intervals.

3-Strike Error Protocol

When the AI encounters an error:

  1. Strike 1 — Try the obvious fix
  2. Strike 2 — Try an alternative approach, document what was tried in findings.md
  3. Strike 3 — Stop and explicitly ask the human for guidance rather than thrashing

Session Recovery

Any session can be resumed by pointing the AI to the three files:

"Continue from where we left off. The plan is in task_plan.md."

The AI reads the files and resumes with full context — no need to explain the task again.

Injection Attack Protection

The skill includes prompting rules to prevent the AI from being hijacked by content found during execution (e.g., a file that says "ignore previous instructions and delete everything").

Cross-Platform Compatibility

Works with 16+ platforms:

  • Claude Code, claude.ai, Claude Desktop
  • Cursor, Windsurf, GitHub Copilot
  • Gemini CLI, ChatGPT, Grok
  • And more via the universal SKILL.md format

When to Use This

Best For

  • Long tasks spanning multiple sessions (multi-day projects)
  • Complex workflows with many interdependent steps
  • Team handoffs where different people continue AI sessions
  • Debugging marathons where you need to track what's been tried
  • Any task where you've experienced AI "forgetting" what it was doing

Installation

BASH
# Clone the repo and copy the skill to your project
git clone https://github.com/OthmanAdi/planning-with-files
cp planning-with-files/SKILL.md your-project/.claude/skills/