Masterclass Guide to Plan and Prepare for Penetration Testing (updated ) , Penetration testing (pentesting) is a critical security practice that helps identify vulnerabilities in systems, networks, and applications before attackers exploit them. Proper planning and preparation ensure a smooth and effective pentest. Below is a structured, article-wise breakdown of the process.
1. Define Objectives & Scope
a. Determine Goals
Compliance requirements (PCI DSS, ISO 27001, GDPR).
Security validation (identify vulnerabilities before attackers do).
Risk assessment (evaluate impact of potential breaches).
b. Establish Scope
In-Scope Systems: Web apps, APIs, networks, cloud services.
Out-of-Scope Systems: Critical production servers (unless explicitly allowed).
Rules of Engagement (RoE):
Allowed techniques (e.g., SQLi, brute force).
Prohibited actions (e.g., DDoS, data corruption).
c. Legal & Compliance Considerations
Get Written Authorization (signed contract).
Non-Disclosure Agreement (NDA).
Statement of Work (SOW) detailing timelines, methods, and deliverables.
2. Choose the Right Pentest Approach
a. Testing Type
Black Box (no prior knowledge, simulates external hackers).
Gray Box (limited access, mimics insider threats).
White Box (full access, including source code).
b. Automated vs. Manual Testing
Automated Scans (Nessus, Burp Suite, OpenVAS) for quick vulnerability detection.
Manual Testing for advanced exploits (business logic flaws, zero-days).
c. Select Pentesting Team
In-House Team (if skilled in security testing).
External Pentesters (certified professionals like OSCP, CEH).
3. Pre-Engagement Preparation
a. Gather Documentation
Network diagrams, IP ranges, API documentation.
User roles & access levels (for privilege escalation testing).
b. Set Up a Safe Testing Environment
Use Staging/Test Systems (avoid production risks).
Take Backups (in case of accidental disruptions).
c. Notify Stakeholders
IT team (to avoid false alarms from IDS/IPS).
Management (for approval and awareness).
Incident Response Team (in case of unexpected issues).
4. Conduct the Penetration Test
a. Reconnaissance (Information Gathering)
Passive Recon: WHOIS, DNS lookups, OSINT (Google dorking).
Active Recon: Port scanning (Nmap), service enumeration.
b. Vulnerability Scanning & Exploitation
Scan for Weaknesses: Use tools like Nessus, Burp Suite, Metasploit.
Exploit Vulnerabilities: Test SQLi, XSS, RCE, misconfigurations.
c. Post-Exploitation (If in Scope)
Privilege escalation.
Lateral movement (accessing other systems).
Data exfiltration simulation.
d. Maintain Stealth (Avoid Detection)
Bypass WAFs, IDS/IPS.
Clear logs (if permitted).
5. Post-Pentest Best Practices
Continuous Testing: Schedule regular pentests (annually or after major updates).
Security Awareness Training: Educate employees on phishing, social engineering.
Improve Incident Response: Update IR plans based on findings.
Incoclusion
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