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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.

日本語の概要は準備中です。原文の説明を表示しています。

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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

TypePurposeScope
External PentestAssess external attack surfacePublic-facing systems
Internal PentestAssess insider threat riskInternal network
Web ApplicationFind application vulnerabilitiesSpecific applications
Social EngineeringTest human securityEmployees, processes
Red TeamFull adversary simulationEntire 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

FactorConsideration
Asset ValueHigher value = higher investment
ComplexityMore systems = more time
Depth RequiredThorough testing costs more
Reputation ValueBrand-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:

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:

FactorQuestions to Ask
ExperienceYears in field, similar projects
MethodologyOWASP, PTES, custom approach
ReportingSample reports, detail level
CommunicationAvailability, update frequency

Define Methodology

  • Select testing standard - PTES, OWASP, NIST
  • Determine access level - Black box, gray box, white box
  • Agree on techniques - Manual vs. automated testing
  • Set communication schedule - Updates and escalation

Testing Approaches:

TypeAccess LevelSimulates
Black BoxNo informationExternal attacker
Gray BoxPartial accessInsider with limited access
White BoxFull accessInsider/detailed audit

Define Report Format

  • Review sample reports - Ensure quality meets needs
  • Specify required sections - Executive summary, technical details
  • Request machine-readable output - CSV, XML for tracking
  • Agree on risk ratings - CVSS, custom scale

Report Should Include:

  • Executive summary for management
  • Technical findings with evidence
  • Risk ratings and prioritization
  • Remediation recommendations
  • Retesting guidance

Phase 4: Monitoring

Implement Security Monitoring

  • Deploy IDS/IPS - Intrusion detection systems
  • Enable logging - Comprehensive audit trails
  • Configure SIEM - Centralized log analysis
  • Set up alerting - Real-time notifications

Monitoring Tools:

# Check security logs
tail -f /var/log/auth.log
tail -f /var/log/apache2/access.log

# Monitor network
tcpdump -i eth0 -w capture.pcap

Configure Logging

  • Centralize logs - Aggregate from all systems
  • Set retention periods - Keep logs for analysis
  • Enable detailed logging - Application and system level
  • Test log collection - Verify all sources working

Key Logs to Monitor:

  • Authentication events
  • Application errors
  • Network connections
  • File access
  • System changes

Monitor Exception Tools

  • Track error rates - Unusual spikes indicate testing
  • Brief operations team - Distinguish testing from attacks
  • Document baseline - Normal vs. pentest activity

Watch Security Tools

  • Review IDS alerts - Separate pentest from real attacks
  • Monitor WAF logs - Track blocked attempts
  • Check endpoint protection - Antivirus detections

Phase 5: Remediation

Ensure Backups

  • Verify backup integrity - Test restoration
  • Document recovery procedures - Know how to restore
  • Separate backup access - Protect from testing

Reserve Remediation Time

  • Allocate team availability - Post-pentest analysis
  • Schedule fix implementation - Address findings
  • Plan verification testing - Confirm fixes work

Patch During Testing Policy

  • Generally avoid patching - Maintain consistent environment
  • Exception for critical issues - Security emergencies only
  • Communicate changes - Inform pentesters of any changes

Cleanup Procedure

  • Remove test artifacts - Backdoors, scripts, files
  • Delete test accounts - Remove pentester access
  • Restore configurations - Return to original state
  • Verify cleanup complete - Audit all changes

Schedule Next Pentest

  • Determine frequency - Annual, quarterly, after changes
  • Consider continuous testing - Bug bounty, ongoing assessments
  • Budget for future tests - Plan ahead

Testing Frequency Factors:

  • Release frequency
  • Regulatory requirements
  • Risk tolerance
  • Past findings severity

Quick Reference

Pre-Pentest Checklist

□ Scope defined and documented
□ Authorization obtained
□ Environment prepared
□ Hosting provider notified
□ Team briefed
□ Monitoring enabled
□ Backups verified

Post-Pentest Checklist

□ Report received and reviewed
□ Findings prioritized
□ Remediation assigned
□ Fixes implemented
□ Verification testing scheduled
□ Environment cleaned up
□ Next test scheduled

Constraints

  • Production testing carries inherent risks
  • Budget limitations affect thoroughness
  • Time constraints may limit coverage
  • Tester expertise varies significantly
  • Findings become stale quickly

Examples

Example 1: Quick Scope Definition

**Target:** Corporate web application (app.company.com)
**Type:** Gray box web application pentest
**Duration:** 5 business days
**Excluded:** DoS testing, production database access
**Access:** Standard user account provided

Example 2: Monitoring Setup

# Enable comprehensive logging
sudo systemctl restart rsyslog
sudo systemctl restart auditd

# Start packet capture
tcpdump -i eth0 -w /tmp/pentest_capture.pcap &

Troubleshooting

IssueSolution
Scope creepDocument and require change approval
Testing impacts productionSchedule off-hours, use staging
Findings disputedProvide detailed evidence, retest
Remediation delayedPrioritize by risk, set deadlines
Budget exceededDefine clear scope, fixed-price contracts

When to Use

This skill is applicable to execute the workflow or actions described in the overview.

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