---
name: Planning with Files
slug: planning-with-files-5
category: AI Engineering
description: Planning with Files keeps task plans, findings, and progress in persistent markdown files so work survives context loss and /clear. Use it for multi-step projects, research tasks, or any work requiring many tool calls.
github: "https://github.com/OthmanAdi/planning-with-files/tree/master/skills/planning-with-files"
language: Shell
stars: 26158
forks: 2189
install: "npx degit https://github.com/OthmanAdi/planning-with-files/tree/master/skills/planning-with-files ~/.claude/skills/planning-with-files"
installs_to: ~/.claude/skills/planning-with-files
source_path: skills/planning-with-files/SKILL.md
collection_size: 15
category_size: 2451
collection_url: "https://dirskills.com/collections/OthmanAdi/planning-with-files"
added: 2026-08-14T07:12:02.432Z
last_synced: 2026-08-14T07:12:02.432Z
canonical_url: "https://dirskills.com/skills/planning-with-files-5"
---

# Planning with Files

Planning with Files keeps task plans, findings, and progress in persistent markdown files so work survives context loss and /clear. Use it for multi-step projects, research tasks, or any work requiring many tool calls.

**Install:**

```bash
npx degit https://github.com/OthmanAdi/planning-with-files/tree/master/skills/planning-with-files ~/.claude/skills/planning-with-files
```

## README

# 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:

```bash
# 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)"
```

```powershell
# 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**

| Location | What Goes There |
|----------|-----------------|
| Skill directory (`${CLAUDE_PLUGIN_ROOT}/`) | Templates, scripts, reference docs |
| Your project directory | `task_plan.md`, `findings.md`, `progress.md` |

## 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

| 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

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.

```markdown
## 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

| 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 |
| What am I about to do? | Next Step in task_plan.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](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:

```bash
# 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:

| Install route | What you get | `/plan-goal`, `/plan-loop` available? |
|---|---|---|
| `/plugin marketplace add OthmanAdi/planning-with-files` then `/plugin install` | SKILL.md, scripts, templates, **plus `commands/` folder** | Yes, as `/plan-goal` and `/plan-loop` |
| `npx skills add OthmanAdi/planning-with-files` (or ClawHub) | SKILL.md, scripts, templates only | No, follow the manual fallback below |

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)

For skill-only installs (no `commands/` folder) or sessions where the slash command refuses to fire, the model can produce the same effect by executing the wrapper steps inline.

**Manual `/plan-goal` procedure:**

1. Resolve the active plan: prefer `${PLAN_ID}` env var, then `.planning/.active_plan`, then newest `.planning/<dir>/`, then legacy `./task_plan.md`.
2. Read the resolved `task_plan.md`.
3. Compose a goal condition. Default: `"all phases in task_plan.md report Status: complete and check-complete.sh reports ALL PHASES COMPLETE"`. If the user passed additional clauses, append them.
4. Issue Claude Code's native `/goal <condition>` (CC primitive, always available).
5. Confirm to the user: print the condition + active plan ID + remind that `/goal clear` cancels.
6. Refuse if `task_plan.md` does not exist; direct the user to run init first.

**Manual `/plan-loop` procedure:**

1. Parse args: first arg matching `^\d+[smhd]$` is the interval (default `10m`), remaining args are an optional task prompt.
2. Resolve the active plan as above.
3. Compose the loop tick prompt. If user passed a task prompt, use it verbatim. Otherwise use the planning-aware default that re-reads `task_plan.md` and `progress.md`, runs `scripts/check-complete.sh`, and writes a `progress.md` entry if no progress was logged since the last tick.
4. Issue Claude Code's native `/loop <interval> <prompt>` (CC primitive, always available).
5. Confirm to the user: print interval + active plan ID + remind that bare `/loop` runs the built-in maintenance prompt.

Both procedures match what the `commands/plan-goal.md` and `commands/plan-loop.md` files would have fed the model when invoked. The native `/loop` and `/goal` primitives are always available in Claude Code; only the planning-aware wrapper is plugin-scoped.

### `loop.md` template

Claude Code's bare `/loop` reads `.claude/loop.md` (project) or `~/.claude/loop.md` (user). v2.38 ships a planning-aware template at `templates/loop.md`. Install once:

```bash
# user-wide
cp ${CLAUDE_PLUGIN_ROOT}/templates/loop.md ~/.claude/loop.md

# project-specific
cp ${CLAUDE_PLUGIN_ROOT}/templates/loop.md .claude/loop.md
```

After install, bare `/loop <interval>` runs the planning-aware tick.

## Autonomous and Gated Modes (v3)

v3 adds two opt-in modes for long-running agentic work with strong models (Opus 4.8, Fable 5, GPT 5.5 class). Both key off an explicit marker file in the plan directory. With no marker present, behavior is exactly v2.43: nothing in this section changes the legacy path.

The mode is set by writing a `.mode` file next to the plan (`.planning/<id>/.mode`, or `./.mode` in legacy root mode). `init-session` writes it for you when you pass `--autonomous` or `--gated`.

### The legacy invariant (promise)

With no `.mode` file and no other v3 marker, the hooks produce byte-identical output to v2.43, including the raw `progress.md` tail and the `===BEGIN PLAN DATA===` / `===END PLAN DATA===` delimiters. Every v3 behavior is additive and opt-in. No existing workflow changes.

### What each mode does

| | Legacy (default) | Autonomous | Gated |
|---|---|---|---|
| Turn-start injection (UserPromptSubmit) | Full plan head + raw progress tail | Full plan head + structured ledger summary | Full plan head + structured ledger summary |
| Per-tool-call injection (PreToolUse) | Plan head every call | Dropped (recitation policy) | Dropped (recitation policy) |
| Stop event | Advisory only, never blocks | Advisory only, never blocks | Completion gate may block (host-aware) |
| Attestation | Opt-in | Default-on at init | Default-on at init |
| Progress injection | Raw `tail -20 progress.md` | `ledger-summary.sh` synthesized block | `ledger-summary.sh` synthesized block |

Autonomous mode answers the recitation question: strong models drift less, so the per-tool-call plan re-injection (about 90 tokens per matched tool call, the component that scales with tool use) is dropped. Turn-start injection stays because the evidence (arxiv 2603.03258, claudefa.st on Opus 4.7+ subagents) shows drift is real and the full plan file still matters once per turn. Eliminating recitation entirely is not supported by evidence.

Gated mode adds the completion gate on top of autonomous behavior. The gate is the termination oracle: it judges the plan artifact on disk, not the conversation transcript, which is why it beats a transcript-bound evaluator that can be hallucinated.

### Structure-aware injection (v3.8.0, opt-in)

The default injection is `head -50` (turn start) and `head -30` (per tool call), which is position-blind: late in a long plan the in_progress phase, the Decisions journal, and the Errors table all sit past the injected window, so every injection pays the token cost while the window no longer carries the active phase. Opt in with `PWF_INJECT=smart` in the environment, or an `inject-smart` token in the plan's `.mode` file, and the injection instead emits: the plan title, the Goal / Next Step / Current Phase sections, a phase count, the full first in_progress phase section, and the last 3 rows of Decisions Made. Plans without `### Phase` headings fall back to the plain head. `inject-smart` alone does not activate any other v3 behavior; it composes with autonomous and gated modes (`init-session` mode tokens are space-separated in `.mode`). With neither the env var nor the token present, output is byte-identical to the legacy shape.

### Parallel-write guard (v3.10.0, on by default)

Two sessions sharing one plan directory can both write `task_plan.md` from the same read. The later write silently discards the earlier one's work, and nothing notices: injection, `plan-doctor` and the Stop gate all read the clobbered file as an ordinary edit. Attestation does not cover this. It compares against a baseline a human approved once, it reports a collaborator's edit with the same `[PLAN TAMPERED]` wording as a hostile rewrite, and it is a read-side gate that cannot stop the stale write from landing.

The guard compares progress between turn-start fires rather than hashes. Checked items and completed phases only go up during normal work, so a DECREASE means work that was on disk is gone. Forward motion stays silent, which is what keeps the signal worth reading, and both markers are language-neutral because every translated template keeps the literal English `**Status:** complete` token. On a decrease it prints one advisory line naming how much was lost and pointing at `git diff`, then injects normally. It never blocks: this hook always exits 0 and no host offers a PreToolUse deny path. Archiving completed phases also trips it. Turn it off with `PWF_PLAN_GUARD=0` or a `plan-guard-off` token in `.mode`.

Known ceiling: the marker is keyed on the plan path, not the session, so the warning reaches whichever session fires next rather than specifically the one holding the stale copy. Per-session keying needs `PWF_SESSION_ID`, which most hosts never set.

### Gate decision table

The Stop gate blocks ONLY when all of these hold. Any single failure allows the stop. This is the lesson from issue #178: an incomplete plan is a normal state, not an error, and accidental blocking infuriates users.

1. Mode is ga