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:

# 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