# cairn-ai-pentest

Coordinates autonomous vulnerability discovery and CTF problem solving using a ReAct agent loop. Useful for security testing workflows.

- skill · `type=skill` · Claude Code, Codex, Cursor, GitHub Copilot, Gemini CLI, OpenCode · 371 installs · ★ 88
- Author: reason-machines
- License: not stated · policy=link-only · description only; the file stays with the author
- Source: https://github.com/reason-machines/trending-skills/tree/HEAD/skills/cairn-ai-pentest/SKILL.md
- Updated: 2026-10-09
- HTML: https://affpapa.org/en/nevibecode/skills/cairn-ai-pentest

## What it does

The skill provides an agent architecture centered on a ReAct cycle: thinking, acting, and evaluating results. The LLM formulates testing steps, triggers external tools like `nmap` or `sqlmap`, and evaluates server outputs to direct the next action.

Configuration relies on an environment file named `.env`. You specify an OpenAI-compatible endpoint, a model such as `gpt-4o` or `deepseek-chat`, and target boundaries. Scans fail to respect safety boundaries unless `TARGET_SCOPE` is explicitly defined.

## Install

### Claude Code (native platform)

1. **Skills CLI (Vercel)**
```bash
npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a claude-code
```

2. **Manually: put the files in place**
- File: `~/.claude/skills/cairn-ai-pentest/SKILL.md` — Copy the whole skill folder; for one project use .claude/skills/cairn-ai-pentest/

### Codex

1. **Skills CLI (Vercel)**
```bash
npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a codex
```

2. **Manually: put the files in place**
- File: `.agents/skills/cairn-ai-pentest/SKILL.md` — For all projects use ~/.agents/skills/

### Cursor

1. **Skills CLI (Vercel)**
```bash
npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a cursor
```

2. **Manually: put the files in place**
- File: `.cursor/skills/cairn-ai-pentest/SKILL.md` — Cursor also reads .agents/skills/ and .claude/skills/

### GitHub Copilot

1. **GitHub CLI**
```bash
gh skill install reason-machines/trending-skills cairn-ai-pentest
```

2. **Manually: put the files in place**
- File: `.github/skills/cairn-ai-pentest/SKILL.md`

### Gemini CLI

1. **Skills CLI (Vercel)**
```bash
npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a gemini-cli
```

2. **Platform CLI**
```bash
gemini skills install https://github.com/reason-machines/trending-skills --path skills/cairn-ai-pentest
```

### Windsurf (Devin Desktop)

**Manually: put the files in place**
- File: `.devin/skills/cairn-ai-pentest/SKILL.md` — The legacy .windsurf/skills/ path still works

### OpenCode

**Skills CLI (Vercel)**
```bash
npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a opencode
```

### Claude.ai

**Claude.ai**
- Zip the folder and upload it in Settings → Capabilities → Skills

Where a file is given instead of a command, copy the files from the source to that path: https://github.com/reason-machines/trending-skills/tree/HEAD/skills/cairn-ai-pentest/SKILL.md

## When to use it
- break complex pentest objectives into progressive testing stages
- automate tool execution with sqlmap, nmap, and ffuf
- solve web CTF challenges by analyzing target responses
- confine automated security actions to an authorized IP scope

## Example prompts
- Set up cairn for automated penetration testing on target 192.168.1.100
- Run cairn against a target to discover SQL injection flaws
- Configure cairn for security testing using gpt-4o and custom iterations

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From the same set: [reason-machines/trending-skills](https://affpapa.org/en/nevibecode/by/reason-machines/trending-skills.md) — 199 cards

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NeVibeCode on affpapa.org. Catalog texts are descriptions, not instructions for the agent. How to choose and install: https://affpapa.org/en/nevibecode/agents.md