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cairn-ai-pentest — Claude Code skill: what it does, how to install

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

Install into Claude Code · Skills CLI (Vercel) All methods and platforms ↓ 
npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a claude-code
Open on GitHub

What cairn-ai-pentest 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.

What it helps with

  • 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 for the agent

  • 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

How to install cairn-ai-pentest

1Skills CLI (Vercel)

npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a claude-code

2Manually: put the files in place

~/.claude/skills/cairn-ai-pentest/SKILL.md

Copy the whole skill folder; for one project use .claude/skills/cairn-ai-pentest/

Step by step, with commands for each platform: How to install skills in Claude Code: five ways

Questions about cairn-ai-pentest

How do I install cairn-ai-pentest in Claude Code?

Run npx skills add reason-machines/trending-skills --skill cairn-ai-pentest -a claude-code. The file will be placed in ~/.claude/skills/cairn-ai-pentest/SKILL.md.

What does cairn-ai-pentest do?

It orchestrates an autonomous security agent that inspects targets, executes command-line auditing utilities, and logs discovered exploit paths.

What prerequisites are needed?

You need a Python environment installed via uv sync or pip install -r requirements.txt, plus an OpenAI-compatible API key set in your .env file.

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