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
Ready-to-paste message
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-checklistOr 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.mdTechnical 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:
- Ask the user to state the exact target URL, IP, account, or resource.
- Ask the user to confirm written authorization and the permitted scope.
- Show the exact command(s) and explain their expected effect.
- 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.
Popularity
- GitHub stars
- 48k
- Ranking position
- #3807
- License
- MIT
- Updated
- 10/15/2026
Comments
- …
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