Executing Plans Inline
obra/superpowers
Has the agent carry out an implementation plan itself, task by task in the current session, keeping a ledger, proving each step with a test and ending with one whole-branch review.
Implements file-based planning for complex multi-step tasks.
Install Planning With Files
$ npx skills add trailofbits/skills-curated --skill planning-with-files -a claude-codeProject install by default; add -g for ~/.claude/skills/.
$ gh skill install trailofbits/skills-curated planning-with-files --agent claude-codeProject scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).
$ git clone --depth 1 https://github.com/trailofbits/skills-curated.git skills-src && mkdir -p .claude/skills && cp -r skills-src/plugins/planning-with-files/skills/planning-with-files .claude/skills/planning-with-files && rm -rf skills-srcUse ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.
Claude Code skills documentation · loads skills from .claude/skills/
Install the "planning-with-files" agent skill from https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-files into .claude/skills/planning-with-files/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "planning-with-files", then confirm the skill loads.Claude Code copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$skill-installer install https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-filesType this inside Codex. $skill-installer <name> installs a curated skill from openai/skills. The installer writes to $CODEX_HOME/skills (default ~/.codex/skills). Restart Codex if the skill does not show up.
$ npx skills add trailofbits/skills-curated --skill planning-with-files -a codexProject install goes to .agents/skills/; add -g for ~/.codex/skills/.
$ gh skill install trailofbits/skills-curated planning-with-files --agent codexProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/trailofbits/skills-curated.git skills-src && mkdir -p .agents/skills && cp -r skills-src/plugins/planning-with-files/skills/planning-with-files .agents/skills/planning-with-files && rm -rf skills-srcUse ~/.agents/skills/ instead of .agents/skills for a personal install.
Codex skills documentation · loads skills from .agents/skills/
Install the "planning-with-files" agent skill from https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-files into .agents/skills/planning-with-files/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "planning-with-files", then confirm the skill loads.Codex copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ npx skills add trailofbits/skills-curated --skill planning-with-files -a cursorProject install goes to .agents/skills/; add -g for ~/.cursor/skills/.
$ gh skill install trailofbits/skills-curated planning-with-files --agent cursorProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/trailofbits/skills-curated.git skills-src && mkdir -p .cursor/skills && cp -r skills-src/plugins/planning-with-files/skills/planning-with-files .cursor/skills/planning-with-files && rm -rf skills-srcUse ~/.cursor/skills/ instead of .cursor/skills for a personal install.
Cursor skills documentation · loads skills from .cursor/skills/, .agents/skills/, .claude/skills/, .codex/skills/
Install the "planning-with-files" agent skill from https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-files into .cursor/skills/planning-with-files/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "planning-with-files", then confirm the skill loads.Cursor copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ gemini skills install https://github.com/trailofbits/skills-curated.git --path plugins/planning-with-files/skills/planning-with-files--scope user (default) or --scope workspace; --path is the subfolder of the repo that holds the skill; --consent skips the security confirmation prompt.
$ npx skills add trailofbits/skills-curated --skill planning-with-files -a gemini-cliProject install goes to .agents/skills/; add -g for ~/.gemini/skills/.
$ gh skill install trailofbits/skills-curated planning-with-files --agent gemini-cliProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/trailofbits/skills-curated.git skills-src && mkdir -p .gemini/skills && cp -r skills-src/plugins/planning-with-files/skills/planning-with-files .gemini/skills/planning-with-files && rm -rf skills-srcUse ~/.gemini/skills/ instead of .gemini/skills for a personal install, then run /skills reload.
Gemini CLI skills documentation · loads skills from .gemini/skills/, .agents/skills/
Install the "planning-with-files" agent skill from https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-files into .gemini/skills/planning-with-files/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "planning-with-files", then confirm the skill loads.Gemini CLI copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ gh skill install trailofbits/skills-curated planning-with-filesInstalls for Copilot at project scope by default; add --scope user for a personal install. Preview a skill first with gh skill preview. Needs GitHub CLI 2.90.0 or later (public preview).
$ npx skills add trailofbits/skills-curated --skill planning-with-files -a github-copilotProject install goes to .agents/skills/; add -g for ~/.copilot/skills/.
$ git clone --depth 1 https://github.com/trailofbits/skills-curated.git skills-src && mkdir -p .github/skills && cp -r skills-src/plugins/planning-with-files/skills/planning-with-files .github/skills/planning-with-files && rm -rf skills-srcUse ~/.copilot/skills/ instead of .github/skills for a personal install. Commit .github/skills so cloud agent and code review can use it.
GitHub Copilot skills documentation · loads skills from .github/skills/, .claude/skills/, .agents/skills/
Install the "planning-with-files" agent skill from https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-files into .github/skills/planning-with-files/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "planning-with-files", then confirm the skill loads.GitHub Copilot copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
$ npx skills add trailofbits/skills-curated --skill planning-with-files -a opencodeOpenCode documents no install command of its own. Project install goes to .agents/skills/; add -g for ~/.config/opencode/skills/.
$ gh skill install trailofbits/skills-curated planning-with-files --agent opencodeProject scope by default (.agents/skills/); add --scope user for a personal install.
$ git clone --depth 1 https://github.com/trailofbits/skills-curated.git skills-src && mkdir -p .opencode/skills && cp -r skills-src/plugins/planning-with-files/skills/planning-with-files .opencode/skills/planning-with-files && rm -rf skills-srcUse ~/.config/opencode/skills/ instead of .opencode/skills for a personal install.
OpenCode skills documentation · loads skills from .opencode/skills/, .claude/skills/, .agents/skills/
Install the "planning-with-files" agent skill from https://github.com/trailofbits/skills-curated/tree/main/plugins/planning-with-files/skills/planning-with-files into .opencode/skills/planning-with-files/ in this project. Copy the whole folder (SKILL.md and every file beside it), keep the folder name "planning-with-files", then confirm the skill loads.OpenCode copies the folder itself, the same result as the manual copy. Check what it changed before you commit it.
Facts
- Skill name
planning-with-files- GitHub stars
- 512
- Token cost
- ~1.5k tokens
- SKILL.md length
- 568 words
- Files
- 4 (incl. references)
- Skills in repo
- 24
- Repo updated
- First seen
- Licence
- CC-BY-SA-4.0
At a glance
Implements file-based planning for complex multi-step tasks.
- Works in 6 steps: Create Plan First → The 2-Action Rule → Read Before Decide → …
- Starting tasks requiring 5 tool calls
- SKILL.md covers Quick Start, When to Use, When NOT to Use and Core Pattern, plus 7 more sections
- Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md
What it does
Planning With Files is an agent skill from trailofbits/skills-curated, published by the product's own GitHub organization. Implements file-based planning for complex multi-step tasks. Creates taskplan.md, findings.md, and progress.md as persistent working memory. Use when starting tasks requiring 5 tool calls, multi-phase projects, research, or any work where losing track of goals and progress would be costly.
Its SKILL.md is about 1.5k tokens, which your agent loads only when the skill is triggered. The skill folder holds 4 other files, including reference files (for example `references/examples.md`, `references/principles.md` and `references/templates.md`).
It sits in Agent Workflows, covering Planning. The repository describes itself as: Curated, community-vetted Claude Code plugin marketplace. The licence is CC-BY-SA-4.0.
When your agent uses it
- Starting tasks requiring 5 tool calls
- Multi-phase projects
- Any work where losing track of goals and progress would be costly
Example prompts
- “Use the planning-with-files skill to implement file-based planning for complex multi-step tasks”
- “/planning-with-files”
Requirements
- Pre-approved tools (allowed-tools): Read, Write, Edit, Glob, Grep
Workflow steps
6 steps, taken from the step headings in SKILL.md.
What it can do on your machine
Read from SKILL.md and the folder at commit 6d05be4. It shows what the files ask for, not the result of running them.
Tool permissions
Pre-approves these tools, so the agent can use them without asking each time:
ReadWriteEditGlobGrep
From allowed-tools in the SKILL.md frontmatter.
Runs code
No scripts in the folder and no shell commands in SKILL.md (its code samples are markdown).
From the folder's file list and the shell code blocks in SKILL.md.
Network
No URLs in SKILL.md.
From URLs in SKILL.md, links to its own repository left out.
Credentials
Names no API keys, tokens, secrets or passwords.
From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.
Context cost
Planning With Files loads about 1.5k tokens when it runs, and up to ~3.4k if it reads all its reference files. Until then it costs about 78 tokens; SKILL.md has 568 words of instructions outside code blocks.
Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.
Safety
Auto-check passed
The automated check found no risky patterns in SKILL.md.
Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.
SKILL.md
The full file from trailofbits/skills-curated at commit 6d05be4, republished under its CC-BY-SA-4.0 licence (© trailofbits). 568 words, ~1,464 tokens.
Download SKILL.mdSave it as
.claude/skills/planning-with-files/SKILL.md (or your agent's skills folder). This skill also uses 3 other files; get the full folder from GitHub.- name
- planning-with-files
- description
- Implements file-based planning for complex multi-step tasks. Creates task_plan.md, findings.md, and progress.md as persistent working memory. Use when starting tasks requiring >5 tool calls, multi-phase projects, research, or any work where losing track of goals and progress would be costly.
- allowed-tools
- Read, Write, Edit, Glob, Grep
Planning with Files
Use persistent markdown files as working memory on disk.
Quick Start
- Create planning files -- use
/planor create manually from templates - Create
task_plan.mdwith goal, phases, and key questions - Create
findings.mdfor research and decisions - Create
progress.mdfor session logging - Re-read the plan before decisions -- refreshes goals in attention
- Update after each phase -- mark status, log errors
When to Use
- Multi-step tasks (3+ phases)
- Research projects requiring many searches
- Building or creating projects with multiple files
- Tasks spanning many tool calls (>10)
- Any work where losing track of goals would be costly
- Tasks that may span multiple sessions
When NOT to Use
- Simple questions or quick lookups
- Single-file edits with obvious scope
- Tasks completable in under 5 tool calls
- Conversational exchanges without implementation
Core Pattern
Context Window = RAM (volatile, limited)
Filesystem = Disk (persistent, unlimited)
Anything important gets written to disk.After many tool calls, the original goal drifts out of the attention
window. Reading task_plan.md brings it back. This is the single
most important pattern in file-based planning.
File Purposes
| File | Purpose | When to Update |
|---|---|---|
task_plan.md | Phases, progress, decisions | After each phase completes |
findings.md | Research, discoveries, decisions | After ANY discovery |
progress.md | Session log, test results | Throughout the session |
All three files go in the project root, not the plugin directory.
Critical Rules
1. Create Plan First
Never start a complex task without task_plan.md. This is
non-negotiable. The plan is your persistent memory.
2. The 2-Action Rule
After every 2 search, browse, or read operations, immediately save
key findings to findings.md. Multimodal content (images, browser
results, PDF contents) does not persist in context -- capture it as
text before it is lost.
3. Read Before Decide
Before any major decision, re-read task_plan.md. This pushes
goals and context back into the recent attention window, counteracting
the "lost in the middle" effect that occurs after ~50 tool calls.
[Original goal -- far away in context, forgotten]
...many tool calls...
[Recently read task_plan.md -- gets ATTENTION]
→ Now make the decision with goals fresh in context4. Update After Act
After completing any phase:
- Mark phase status:
in_progress->complete - Log any errors encountered in the Errors table
- Note files created or modified in
progress.md
5. Log ALL Errors
Every error goes in task_plan.md. Include the attempt number and
resolution. This builds knowledge and prevents repeating failures.
## Errors Encountered
| Error | Attempt | Resolution |
|-------|---------|------------|
| FileNotFoundError | 1 | Created default config |
| API timeout | 2 | Added retry logic |Show full SKILL.md (220 more words)Show less
6. Never Repeat Failures
If an action failed, the next action must be different. Track what you tried and mutate the approach.
if action_failed:
next_action != same_action3-Strike Error Protocol
ATTEMPT 1: Diagnose & Fix
-> Read error carefully
-> Identify root cause
-> Apply targeted fix
ATTEMPT 2: Alternative Approach
-> Same error? Try a different method
-> Different tool? Different library?
-> NEVER repeat the 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 (with attempt log)
-> Share the specific error
-> Ask for guidanceRead vs Write Decision Matrix
| Situation | Action | Reason |
|---|---|---|
| Just wrote a file | Don't read it | Content still in context |
| Viewed image/PDF | Write findings NOW | Multimodal content doesn't persist |
| Browser returned data | Write to file | Screenshots don't persist |
| Starting new phase | Read plan/findings | Re-orient if context is stale |
| Error occurred | Read relevant file | Need current state to fix |
| Resuming after gap | Read all planning files | Recover full state |
5-Question Reboot Test
If you can answer these from your planning files, context 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 |
Anti-Patterns
| Don't | Do Instead |
|---|---|
| State goals once and forget | Re-read plan before decisions |
| Hide errors and retry silently | Log every error 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 plugin directory | Create files in project root |
References
- Templates -- starter templates for all three planning files
- Principles -- context engineering principles behind this approach
- Examples -- concrete examples and error recovery patterns
© trailofbits, CC-BY-SA-4.0. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file
Files
SKILL.md and 3 other files (references) in plugins/planning-with-files/skills/planning-with-files of trailofbits/skills-curated.
- SKILL.md
- references/examples.md
- references/principles.md
- references/templates.md
Open the folder on GitHubat commit 6d05be4
Compare with similar skills
Planning With Files next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.
| Skill | Stars | Used in | Tokens | Auto-check | Licence | Repo updated |
|---|---|---|---|---|---|---|
| Planning With Files this skilltrailofbits/skills-curated | 512 | — | ~1.5k | Automated safety check: Pass | CC-BY-SA-4.0 | |
| Executing Plans Inlineobra/superpowers | 296k | 2 repos | ~5.1k | Automated safety check: Pass | MIT | |
| Interview Meaddyosmani/agent-skills | 103k | 6 repos | ~3.8k | Automated safety check: Pass | MIT | |
| OpenSpec Guided OnboardingFission-AI/OpenSpec | 71k | 1 repos | ~4.5k | Automated safety check: Pass | MIT | |
| Writing Plansgeeksblabla/stateofdev.ma | 163 | 57 repos | ~661 | Automated safety check: Pass | None | |
| Subagent Driven DevelopmentAsvarox/allkaraoke | 261 | 38 repos | ~1.2k | Automated safety check: Pass | None |
Similar skills
Interview Me
addyosmani/agent-skills
Asks one question at a time, each with a best guess attached, until the agent is about 95 percent sure what you really want, before any plan, spec or code.
OpenSpec Guided Onboarding
Fission-AI/OpenSpec
Walks you through a complete OpenSpec workflow cycle with narration while doing real work in your codebase.
Writing Plans
geeksblabla/stateofdev.ma
A skill your agent uses when design is complete and you need detailed implementation tasks for engineers with zero codebase context - creates comprehensive implementation plans with exact file…
Subagent Driven Development
Asvarox/allkaraoke
A skill your agent uses when executing implementation plans with independent tasks in the current session
Planning With Files
jd-opensource/JoySafeter
Implements Manus-style file-based planning for complex tasks.
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Categories
Questions about Planning With Files
What does Planning With Files do?
Implements file-based planning for complex multi-step tasks. Planning With Files is an agent skill from trailofbits/skills-curated, published by the product's own GitHub organization. Implements file-based planning for complex multi-step tasks.
When should I use Planning With Files?
Planning With Files fits situations like: starting tasks requiring 5 tool calls; multi-phase projects; any work where losing track of goals and progress would be costly.
How do I install Planning With Files in Claude Code?
Run `npx skills add trailofbits/skills-curated --skill planning-with-files -a claude-code`. Or copy the skill folder (plugins/planning-with-files/skills/planning-with-files in trailofbits/skills-curated) into .claude/skills/planning-with-files in your project. Claude Code loads it when a task matches its description.
How do I install Planning With Files in Codex?
Run `npx skills add trailofbits/skills-curated --skill planning-with-files -a codex`. Or copy the skill folder (plugins/planning-with-files/skills/planning-with-files in trailofbits/skills-curated) into .agents/skills/planning-with-files in your project. Codex loads it when a task matches its description.
Can I use Planning With Files in Cursor, Gemini CLI or GitHub Copilot?
Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add trailofbits/skills-curated --skill planning-with-files -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/planning-with-files, .gemini/skills/planning-with-files, .github/skills/planning-with-files and .opencode/skills/planning-with-files in your project.
What does Planning With Files need to run?
SKILL.md names no scripts, command-line tools or credentials: Planning With Files is instructions for the agent only. Its frontmatter pre-approves these tools: Read, Write, Edit, Glob, Grep.
Does Planning With Files access the network?
SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.
Is Planning With Files safe to install?
Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.
What licence does Planning With Files use?
Planning With Files is published under the CC-BY-SA-4.0 licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.
How many tokens does Planning With Files use?
About 1.5k tokens (SKILL.md is roughly 5.9k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full. Its references folder adds about 1.9k tokens, read only when the agent opens those files.
What are the alternatives to Planning With Files?
Skills that share tags, products or a category with Planning With Files: Executing Plans Inline (obra/superpowers, 296k stars), Interview Me (addyosmani/agent-skills, 103k stars), OpenSpec Guided Onboarding (Fission-AI/OpenSpec, 71k stars) and Writing Plans (geeksblabla/stateofdev.ma, 163 stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.
Who maintains Planning With Files?
trailofbits (a GitHub organization, an official publisher) maintains it in trailofbits/skills-curated, which has 512 GitHub stars. The repository holds 24 skills in this directory. The repository was last updated on July 14, 2026.
Source: trailofbits/skills-curated on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.