# Pentest Checklist

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

- Skill: `ranbot-ai/pentest-checklist` (Agent Skill)
- Install (CLI): `npx skillmds add ranbot-ai/pentest-checklist`
- Raw SKILL.md: https://api.skillmd.com/api/skills/ranbot-ai/pentest-checklist/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: ranbot-ai (https://skillmd.com/u/ranbot-ai)
- Updated: 2026-09-08
- Page: https://skillmd.com/skills/ranbot-ai/pentest-checklist

---



> 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:**
```bash
# 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
- [ ] **Document data handling rules** - Sensitive data procedures
- [ ] **Confirm legal authorization** - Get written permission

#### Notify Hosting Provider

- [ ] **Check provider policies** - What testing is allowed?
- [ ] **Submit authorization requests** - AWS, Azure, GCP requirements
- [ ] **Document approvals** - Keep records

**Cloud Provider Policies:**
- AWS: https://aws.amazon.com/security/penetration-testing/
- Azure: https://docs.microsoft.com/security/pentest
- GCP: https://cloud.google.com/security/overview

#### Freeze Developments

- [ ] **Stop deployments during testing** - Maintain consistent environment
- [ ] **Document current versions** - Record system states
- [ ] **Avoid critical patches** - Unless security emergency

### Phase 3: Expertise Selection

#### Find Qualified Pentesters

- [ ] **Seek recommendations** - Ask trusted sources
- [ ] **Verify credentials** - OSCP, GPEN, CEH, CREST
- [ ] **Check references** - Talk to previous clients
- [ ] **Match expertise to scope** - Web, network, mobile specialists

**Evaluation Criteria:**

| Factor | Questions to Ask |
|--------|------------------|
| Experience | Years in field, similar projects |
| Methodology | OWASP, PTES, custom approach |
| Reporting | Sample reports, detail level |
| Communication | Availability, update frequency |

#### Define Methodology

- [ ] **Select testing standard