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

⚠️ 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: 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: 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 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: Type Access Level Simulates Black Box No information External attacker Gray Box Partial access Insider with limited access White Box Full access Insider/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: 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 Post Pentest Checklist 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 Example 2: Monitoring Setup Troubleshooting Issue Solution Scope creep Document and require change approval Testing impacts production Schedule off hours, use staging Findings disputed Provide detailed evidence, retest Remediation delayed Prioritize by risk, set deadlines Budget exceeded Define clear scope, fixed price contracts When to Use This skill is applicable to execute the workflow or actions described in the overview.

pentest-checklist