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Security48k · #3807

pentest-checklist

Teaches your AI agent to protect apps against attacks and test code and catch bugs before users do.

What it does

This tool helps organize the planning and execution of security tests (pentests). It provides a step-by-step guide to ensure everything is done correctly, from preparation to fixing identified issues.

When to use it

  • ✓Before starting a security test on a system.
  • ✓To ensure all important points of a pentest are covered.
  • ✓When documenting the process of a security test.

Example of what to ask your AI

“Generate a checklist for planning a web application pentest.”

Want more? Open the sections below.

How to use

The easiest way: copy the message below and paste it into Claude, ChatGPT, Cursor or any AI. It reads the skill and follows the instructions.

Skill link

https://github.com/sickn33/agentic-awesome-skills/blob/main/plugins/agentic-awesome-skills-claude/skills/pentest-checklist/SKILL.md

Ready-to-paste message

Use this skill to help me: https://github.com/sickn33/agentic-awesome-skills/blob/main/plugins/agentic-awesome-skills-claude/skills/pentest-checklist/SKILL.md Read the SKILL.md file at that link and follow its instructions for my task.
How it works

The tool acts as an interactive guide, presenting checklists and questions to help the user define the scope, prepare the environment, and select the right experts for a security test.

Installation

Easiest way: copy the skill link and paste it into Claude, ChatGPT or Cursor asking it to follow the instructions.

In the terminal (Claude Code, Codex, Cursor), in your project folder:

npx skills add sickn33/agentic-awesome-skills --skill pentest-checklist

Or download just the file:

curl -L https://raw.githubusercontent.com/sickn33/agentic-awesome-skills/main/plugins/agentic-awesome-skills-claude/skills/pentest-checklist/SKILL.md -o SKILL.md
Technical content (original SKILL.md)

Original text by the author, straight from GitHub.

⚠️ AUTHORIZED USE ONLY This skill is for educational purposes or authorized security assessments only. You must have explicit, written permission from the system owner before using this tool. Misuse of this tool is illegal and strictly prohibited.

Mandatory confirmation gate Before running any command that probes, exploits, changes, persists on, extracts data from, or attempts credential access against a target:

  1. Ask the user to state the exact target URL, IP, account, or resource.
  2. Ask the user to confirm written authorization and the permitted scope.
  3. Show the exact command(s) and explain their expected effect.
  4. Wait for explicit confirmation in the current conversation.

Without that confirmation, remain read-only and provide defensive guidance only. Prefer a sandbox, disposable VM, or controlled lab.

AUTHORIZED USE ONLY: Use this skill only for authorized security assessments, defensive validation, or controlled educational environments.

Pentest Checklist

Purpose

Provide a comprehensive checklist for planning, executing, and following up on penetration tests. Ensure thorough preparation, proper scoping, and effective remediation of discovered vulnerabilities.

Inputs/Prerequisites

  • Clear business objectives for testing
  • Target environment information
  • Budget and timeline constraints
  • Stakeholder contacts and authorization
  • Legal agreements and scope documents

Outputs/Deliverables

  • Defined pentest scope and objectives
  • Prepared testing environment
  • Security monitoring data
  • Vulnerability findings report
  • Remediation plan and verification

Core Workflow

Phase 1: Scope Definition

Define Objectives

  • Clarify testing purpose - Determine goals (find vulnerabilities, compliance, customer assurance)
  • Validate pentest necessity - Ensure penetration test is the right solution
  • Align outcomes with objectives - Define success criteria

Reference Questions:

  • Why are you doing this pentest?
  • What specific outcomes do you expect?
  • What will you do with the findings?

Know Your Test Types

Type Purpose Scope
External Pentest Assess external attack surface Public-facing systems
Internal Pentest Assess insider threat risk Internal network
Web Application Find application vulnerabilities Specific applications
Social Engineering Test human security Employees, processes
Red Team Full adversary simulation Entire organization

Enumerate Likely Threats

  • Identify high-risk areas - Where could damage occur?
  • Assess data sensitivity - What data could be compromised?
  • Review legacy systems - Old systems often have vulnerabilities
  • Map critical assets - Prioritize testing targets

Define Scope

  • List in-scope systems - IPs, domains, applications
  • Define out-of-scope items - Systems to avoid
  • Set testing boundaries - What techniques are allowed?
  • Document exclusions - Third-party systems, production data

Budget Planning

Factor Consideration
Asset Value Higher value = higher investment
Complexity More systems = more time
Depth Required Thorough testing costs more
Reputation Value Brand-name firms cost more

Budget Reality Check:

  • Cheap pentests often produce poor results
  • Align budget with asset criticality
  • Consider ongoing vs. one-time testing

Phase 2: Environment Preparation

Prepare Test Environment

  • Production vs. staging decision - Determine where to test
  • Set testing limits - No DoS on production
  • Schedule testing window - Minimize business impact
  • Create test accounts - Provide appropriate access levels

Environment Options:

Production  - Realistic but risky
Staging     - Safer but may differ from production
Clone       - Ideal but resource-intensive

Run Preliminary Scans

  • Execute vulnerability scanners - Find known issues first
  • Fix obvious vulnerabilities - Don't waste pentest time
  • Document existing issues - Share with testers

Common Pre-Scan Tools:

# Network vulnerability scan
nmap -sV --script vuln TARGET

# Web vulnerability scan
nikto -h http://TARGET

Review Security Policy

  • Verify compliance requirements - GDPR, PCI-DSS, HIPAA

…

FAQ

What is a pentest?

A pentest is a simulated cyber attack to find security flaws in systems, networks, or applications.

Why do I need authorization to use this tool?

Security testing without permission is illegal. This tool should only be used on systems for which you have explicit written authorization.

What are the types of pentests?

There are several types, such as external tests (outside the network), internal tests (inside the network), web application tests, social engineering (deceiving people), and Red Team (full attack simulation).

Details

Original description by the author

Provide a comprehensive checklist for planning, executing, and following up on penetration tests. Ensure thorough preparation, proper scoping, and effective remediation of discovered vulnerabilities.

repo: sickn33/agentic-awesome-skills

Popularity

GitHub stars
48k
Ranking position
#3807
License
MIT
Updated
10/15/2026

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