Planning With Files Skill for Cursor

Planning with Files

Work like Manus: Use persistent markdown files as your "working memory on disk."

FIRST: Check for Previous Session (v2.2.0)

Before starting work, check for unsynced context from a previous session:

# Linux/macOS (auto-detects python3 or python)
$(command -v python3 || command -v python) .cursor/skills/planning-with-files/scripts/session-catchup.py "$(pwd)"

# Windows PowerShell
python "$env:USERPROFILE\.cursor\skills\planning-with-files\scripts\session-catchup.py" (Get-Location)

If catchup report shows unsynced context:

• Run git diff --stat to see actual code changes
• Read current planning files
• Update planning files based on catchup + git diff
• Then proceed with task

Important: Where Files Go

• Templates are in .cursor/skills/planning-with-files/templates/
• Your planning files go in your project directory

| Location | What Goes There |

|----------|-----------------|

| Skill directory (.cursor/skills/planning-with-files/) | Templates, scripts, reference docs |

| Your project directory | task_plan.md, findings.md, progress.md |

Quick Start

Before ANY complex task:

• Create task_plan.md — Use templates/task_plan.md as reference
• Create findings.md — Use templates/findings.md as reference
• Create progress.md — Use templates/progress.md as reference
• Re-read plan before decisions — Refreshes goals in attention window
• Update after each phase — Mark complete, log errors

> Note: Planning files go in your project root, not the skill installation folder.

The Core Pattern

Context Window = RAM (volatile, limited)
Filesystem = Disk (persistent, unlimited)

→ Anything important gets written to disk.

File Purposes

| File | Purpose | When to Update |

|------|---------|----------------|

| task_plan.md | Phases, progress, decisions | After each phase |

| findings.md | Research, discoveries | After ANY discovery |

| progress.md | Session log, test results | Throughout session |

Critical Rules

1. Create Plan First

Never start a complex task without task_plan.md. Non-negotiable.

2. The 2-Action Rule

> "After every 2 view/browser/search operations, IMMEDIATELY save key findings to text files."

This prevents visual/multimodal information from being lost.

3. Read Before Decide

Before major decisions, read the plan file. This keeps goals in your attention window.

4. Update After Act

After completing any phase:

• Mark phase status: in_progress → complete
• Log any errors encountered
• Note files created/modified

5. Log ALL Errors

Every error goes in the plan file. This builds knowledge and prevents repetition.

## Errors Encountered
| Error | Attempt | Resolution |
|-------|---------|------------|
| FileNotFoundError | 1 | Created default config |
| API timeout | 2 | Added retry logic |

6. Never Repeat Failures

if action_failed:
    next_action != same_action

Track what you tried. Mutate the approach.

The 3-Strike Error Protocol

ATTEMPT 1: Diagnose & Fix
  → Read error carefully
  → Identify root cause
  → Apply targeted fix

ATTEMPT 2: Alternative Approach
  → Same error? Try different method
  → Different tool? Different library?
  → NEVER repeat exact same failing action

ATTEMPT 3: Broader Rethink
  → Question assumptions
  → Search for solutions
  → Consider updating the plan

AFTER 3 FAILURES: Escalate to User
  → Explain what you tried
  → Share the specific error
  → Ask for guidance

Read vs Write Decision Matrix

| Situation | Action | Reason |

|-----------|--------|--------|

| Just wrote a file | DON'T read | Content still in context |

| Viewed image/PDF | Write findings NOW | Multimodal → text before lost |

| Browser returned data | Write to file | Screenshots don't persist |

| Starting new phase | Read plan/findings | Re-orient if context stale |

| Error occurred | Read relevant file | Need current state to fix |

| Resuming after gap | Read all planning files | Recover state |

The 5-Question Reboot Test

If you can answer these, your context management is solid:

| Question | Answer Source |

|----------|---------------|

| Where am I? | Current phase in task_plan.md |

| Where am I going? | Remaining phases |

| What's the goal? | Goal statement in plan |

| What have I learned? | findings.md |

| What have I done? | progress.md |

When to Use This Pattern

Use for:

• Multi-step tasks (3+ steps)
• Research tasks
• Building/creating projects
• Tasks spanning many tool calls
• Anything requiring organization

Skip for:

• Simple questions
• Single-file edits
• Quick lookups

Templates

Copy these templates to start:

• templates/task_plan.md — Phase tracking
• templates/findings.md — Research storage
• templates/progress.md — Session logging

Scripts

Helper scripts for automation:

• scripts/init-session.sh — Initialize all planning files
• scripts/check-complete.sh — Verify all phases complete
• scripts/session-catchup.py — Recover context from previous session (v2.2.0)

Advanced Topics

• Manus Principles: See reference.md
• Real Examples: See examples.md

Anti-Patterns

| Don't | Do Instead |

|-------|------------|

| Use TodoWrite for persistence | Create task_plan.md file |

| State goals once and forget | Re-read plan before decisions |

| Hide errors and retry silently | Log errors to plan file |

| Stuff everything in context | Store large content in files |

| Start executing immediately | Create plan file FIRST |

| Repeat failed actions | Track attempts, mutate approach |

| Create files in skill directory | Create files in your project |