Planning with Files Skill

Planning with Files

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

FIRST: Restore Context (v2.2.0)

Before doing anything else, check if planning files exist and read them:

1. If task_plan.md exists, read task_plan.md, progress.md, and findings.md immediately.
2. Then check for unsynced context from a previous session:

# Linux/macOS — auto-detects skill directory (plugin env or default install path)
SKILL_DIR="${CLAUDE_PLUGIN_ROOT:-$HOME/.claude/skills/planning-with-files}"
$(command -v python3 || command -v python) "${SKILL_DIR}/scripts/session-catchup.py" "$(pwd)"

# Windows PowerShell
& (Get-Command python -ErrorAction SilentlyContinue).Source "$env:USERPROFILE\.claude\skills\planning-with-files\scripts\session-catchup.py" (Get-Location)

If catchup report shows unsynced context:

1. Run git diff --stat to see actual code changes
2. Read current planning files
3. Update planning files based on catchup + git diff
4. Then proceed with task

Important: Where Files Go

• Templates are in ${CLAUDE_PLUGIN_ROOT}/templates/
• Your planning files go in your project directory

Quick Start

Before ANY complex task:

1. Create `task_plan.md` — Use [templates/task_plan.md](templates/task_plan.md) as reference
2. Create `findings.md` — Use [templates/findings.md](templates/findings.md) as reference
3. Create `progress.md` — Use [templates/progress.md](templates/progress.md) as reference
4. Re-read plan before decisions — Refreshes goals in attention window
5. 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

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

Whenever a phase status changes, also refresh ## Next Step in task_plan.md so it names the single next action.

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.

7. Continue After Completion

When all phases are done but the user requests additional work:

• Add new phases to task_plan.md (e.g., Phase 6, Phase 7)
• Log a new session entry in progress.md
• Continue the planning workflow as normal

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

The 5-Question Reboot Test

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

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](templates/task_plan.md) — Phase tracking
• [templates/findings.md](templates/findings.md) — Research storage
• [templates/progress.md](templates/progress.md) — Session logging

Scripts

Helper scripts for automation:

• scripts/init-session.sh — Initialize planning files. With a name arg, creates an isolated plan under .planning/YYYY-MM-DD-<slug>/ for parallel task workflows. Without args, writes task_plan.md at project root (legacy mode, backward-compatible).
• scripts/set-active-plan.sh — Switch the active plan pointer (.planning/.active_plan). Run with a plan ID to switch; run without args to show which plan is current.
• scripts/resolve-plan-dir.sh — Resolve the active plan directory. Checks $PLAN_ID env var first, then .planning/.active_plan, then newest plan dir by mtime, then falls back to project root (legacy). Used internally by hooks.
• scripts/check-complete.sh — Verify all phases in the active plan are complete.
• scripts/session-catchup.py — Recover context from a previous session after /clear (v2.2.0).
• scripts/attest-plan.sh (and .ps1) — Lock the current task_plan.md content with a SHA-256 attestation (v2.37.0). Hooks then refuse to inject plan content if the file diverges from the attested hash. Use --show to print the stored hash, --clear to remove the attestation. See /plan-attest command.
• scripts/plan-doctor.sh — One-pass self-check for the mechanisms that fail silently (v3.6.0): plan resolution, hook injection, canonicalizer path shape, attestation state, install surfaces, per-fire hook latency. Run it whenever hooks seem quiet or after installing on a new machine. See /plan-doctor command.

Parallel task workflow

When working on multiple tasks in the same repo simultaneously:

# Start task A
./scripts/init-session.sh "Backend Refactor"
# → .planning/2026-01-10-backend-refactor/task_plan.md

# Start task B in a second terminal
./scripts/init-session.sh "Incident Investigation"
# → .planning/2026-01-10-incident-investigation/task_plan.md

# Switch active plan
./scripts/set-active-plan.sh 2026-01-10-backend-refactor

# Or pin a terminal to a specific plan
export PLAN_ID=2026-01-10-backend-refactor

# Or pin a thread to a project root, when the shell's cwd is somewhere else
export PWF_PLAN_ROOT=/workspace/project

Each session reads from its own isolated plan directory. Hooks resolve the correct plan automatically.

Shared parent directories (v3.9.0)

PLAN_ID is a slug resolved against the current directory, so it can only ever name a plan under $(pwd)/.planning. When an agent thread runs with its cwd at a shared parent (/workspace) while the real work lives in a nested project (/workspace/project), the parent's plan is the only one the hooks can see, and it used to be injected on every fire. PWF_PLAN_ROOT takes an absolute path and pins resolution to that root regardless of where the cwd sits. A pin that does not resolve stops injection rather than falling back.

When no pin is set, the plan was picked by the .active_plan pointer or by the newest plan directory, and a project directly below the root carries its own planning state, the hooks treat that as ambiguous and inject nothing:

[planning-with-files] Ambiguous plan: this cwd has an active plan and a nested
project below it has its own (project). Nothing injected. Pin the thread with
PWF_PLAN_ROOT=<absolute path> or PLAN_ID=<slug>.

Naming the plan explicitly, with either variable or an attached session, skips that check. Detection looks one directory deep, so a project nested further down is not detected.

• scripts/session-catchup.py — Recover context from previous session (v2.2.0). For OpenCode (v2.38.0+), reads the new SQLite store at ${XDG_DATA_HOME:-~/.local/share}/opencode/opencode.db instead of the legacy JSON tree.

Claude Code Turn-Loop Integration (v2.38.0+)

Claude Code shipped three new turn-loop primitives in May 2026: /loop (v2.1.72), /goal (v2.1.139), and the PreCompact hook event. v2.38.0 wires the planning workflow into all three.

Install scope: plugin vs skill-only (v2.42.0 clarification)

Not every install path ships every surface in this section. Two distinct install routes exist:

The PreCompact hook is registered in the SKILL.md frontmatter and works for both routes. The /plan-goal and /plan-loop slash commands live in commands/ at the repo root, which only the plugin route copies into ~/.claude/plugins/marketplaces/. Skill-only installs land at ~/.claude/skills/planning-with-files/ and do not see commands/.

Both slash commands also carry disable-model-invocation: true, which means the model will not auto-trigger them. You type them. Per known Claude Code behavior (anthropics/claude-code issues #26251, #41417), some sessions interpret disable-model-invocation: true as "I cannot use the Skill tool for this entry at all" and refuse to fire even when you type the slash. If that happens, the manual fallback below produces the same effect.

PreCompact hook (auto)

The skill registers a PreCompact hook with matcher "*". It fires on both /compact (manual) and autoCompact (context-full). When task_plan.md is present, the hook:

• Reminds the agent to flush in-context progress to progress.md before compaction completes.
• Prints Plan-SHA256 if an attestation is set, so the post-compaction agent can verify the plan is still the one you approved.
• Stays silent when no plan exists. Exit code 0 always — never blocks compaction.

Compaction still proceeds. The protection model is "the plan is on disk, the plan will be re-read after compaction" — not "the plan survives compaction unchanged in context."

/plan-goal slash command

Composes with Claude Code's /goal. Derives a goal condition from the active plan and forwards it to /goal, so the agent keeps working until the plan file actually reports complete.

/plan-goal                                # default: "all phases report Status: complete"
/plan-goal until all tests pass           # appends user clause to default

/plan-goal does not replace /goal. /goal "anything" still works.

/plan-loop slash command

Composes with Claude Code's /loop. Default 10-minute tick re-reads the planning files, runs check-complete, and writes a progress.md entry if nothing changed since the last tick.

/plan-loop                                # default 10m cadence, default tick prompt
/plan-loop 5m                             # override interval
/plan-loop 15m custom prompt              # override interval + prompt

For a "babysit until done" workflow, combine /plan-loop (cadence) with /plan-goal (termination criterion).

Manual fallback when /plan-goal / /plan-loop are unavailable (v2.42.0)

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