Pentest Plan

Penetration Test Plan

Plan penetration testing for "$ARGUMENTS" covering test type, scope, methodology, rules of engagement, success criteria, and reporting requirements.

Process

1. Define penetration test type:

   • Black box — testers have no prior knowledge of the target (simulates external attacker)
   • Grey box — testers have partial knowledge (user credentials, architecture docs, API documentation)
   • White box — testers have full knowledge (source code, architecture, admin access)
   • Select type based on testing objectives: black box for external threat simulation, grey box for authenticated attack paths, white box for comprehensive coverage
   • Document rationale for selected approach

2. Define scope:

   • In-scope systems — list specific applications, APIs, networks, hosts, and cloud resources to test
   • In-scope test types — network penetration, web application, API, mobile, social engineering, physical
   • Out-of-scope systems — explicitly list systems, networks, or techniques that are excluded
   • Data constraints — define handling of any sensitive data encountered during testing
   • Third-party systems — identify any third-party systems in scope and confirm authorization
   • Document scope boundaries clearly to prevent unauthorized testing

3. Select methodology:

   • OWASP Testing Guide — for web application and API testing
   • PTES (Penetration Testing Execution Standard) — for comprehensive network and application testing
   • NIST SP 800-115 — for government and regulated environments
   • OWASP Mobile Security Testing Guide — for mobile application testing
   • Define testing phases: reconnaissance, scanning, exploitation, post-exploitation, reporting
   • Specify tools permitted and prohibited (if any restrictions apply)

4. Define rules of engagement:

   • Testing windows — permitted hours and days (business hours only, after hours, weekends)
   • Notification — who is aware testing is occurring (security team, SOC, management)
   • Emergency contacts — who to call if testing causes an outage or discovers active breach
   • Prohibited techniques — denial of service (unless explicitly authorized), social engineering of specific individuals, physical intrusion (unless in scope)
   • Data handling — no exfiltration of real customer data, test data only, secure deletion after testing
   • Credential handling — obtained credentials must be reported immediately and not reused outside testing
   • Communication channel — encrypted channel for reporting critical findings during testing
   • Stop conditions — circumstances that require immediate cessation of testing

5. Define success criteria:

   • What constitutes a successful test? (comprehensive coverage, critical findings identified, defense validation)
   • Minimum coverage requirements (percentage of in-scope systems tested, OWASP categories covered)
   • Expected deliverables: executive summary, technical findings, evidence (screenshots, logs), remediation recommendations
   • Finding severity classification aligned with organization's risk framework

6. Define reporting requirements:

   • Executive summary — non-technical overview for leadership
   • Technical findings — detailed vulnerability descriptions with CVSS scores
   • Evidence — proof-of-concept details, screenshots, reproduction steps
   • Risk rating — severity aligned with CVSS and business context
   • Remediation recommendations — specific, actionable guidance per finding
   • Retest plan — scope and timeline for verifying remediation
   • Report delivery: encrypted, limited distribution, defined retention period

7. Set remediation timeline expectations:

   • Critical findings — remediation within 72 hours, retest within 1 week
   • High findings — remediation within 2 weeks, retest within 1 month
   • Medium findings — remediation within 1 month, retest within next scheduled test
   • Low/informational — remediation within 1 quarter, tracked in vulnerability management
   • Define escalation process for overdue remediation

8. Define tester qualifications:

   • Required certifications (OSCP, CEH, GPEN, CREST, or equivalent)
   • Industry experience requirements (years, relevant sectors)
   • Background check and NDA requirements
   • Insurance requirements (professional liability, cyber insurance)
   • Preference for testers with experience in the organization's technology stack

9. Write the artifact to .metapowers/security/$ARGUMENTS/pentest-plan.md with heading:

   Penetration Test Plan

   Include sections:

   • Test Type — selected approach with rationale
   • Scope — in-scope and out-of-scope systems and test types
   • Methodology — selected testing standard and phases
   • Rules of Engagement — testing windows, contacts, prohibited techniques, and stop conditions
   • Success Criteria — coverage requirements and expected deliverables
   • Reporting Requirements — report structure, severity classification, and distribution
   • Remediation Timeline — expected fix timelines per severity level
   • Tester Qualifications — certification, experience, and contractual requirements

Output

The penetration test plan written to .metapowers/security/$ARGUMENTS/pentest-plan.md. Present a summary to the user highlighting:

• Test type and scope definition
• Key rules of engagement and prohibited techniques
• Reporting and remediation timeline expectations
• Tester qualification requirements