Penetration Testing Methodology

Overview

Penetration testing is a systematic approach to evaluating the security of an IT infrastructure by safely attempting to exploit vulnerabilities. This methodology follows industry standards and best practices.

Testing Phases

1. Planning and Reconnaissance

Scope Definition

• Target Systems: Define which systems, networks, and applications are in scope
• Testing Methods: Determine black box, white box, or gray box approach
• Rules of Engagement: Establish testing boundaries and restrictions
• Timeline: Set testing schedule and milestones

Information Gathering (OSINT)

• Passive Reconnaissance: Gather information without direct interaction
  • DNS enumeration
  • WHOIS lookups
  • Social media research
  • Public records search
• Active Reconnaissance: Direct interaction with target systems
  • Port scanning
  • Service enumeration
  • Banner grabbing
  • Network mapping

2. Scanning and Enumeration

Network Discovery

```bash

Network sweep

nmap -sn 192.168.1.0/24

Port scanning

nmap -sS -sV -O target.com

Service enumeration

nmap -sC -sV -p- target.com

UDP scanning

nmap -sU --top-ports 1000 target.com
```

Vulnerability Scanning

• Automated Tools: Nessus, OpenVAS, Qualys
• Manual Testing: Custom scripts and techniques
• Web Application Scanning: Burp Suite, OWASP ZAP
• Database Scanning: SQLMap, NoSQLMap

3. Gaining Access

Exploitation Techniques

• Network Exploits: Buffer overflows, protocol vulnerabilities
• Web Application Exploits: SQL injection, XSS, CSRF
• Social Engineering: Phishing, pretexting, physical access
• Password Attacks: Brute force, dictionary attacks, credential stuffing

Common Exploitation Tools

```bash

Metasploit Framework

msfconsole
use exploit/windows/smb/ms17_010_eternalblue
set RHOSTS target_ip
exploit

SQL Injection with SQLMap

sqlmap -u "http://target.com/page.php?id=1" --dbs

Web shell upload

curl -X POST -F "file=@shell.php" http://target.com/upload.php
```

4. Maintaining Access

Persistence Mechanisms

• Backdoors: Hidden access points for future entry
• Rootkits: Stealth tools to maintain system access
• Scheduled Tasks: Automated execution of malicious code
• Registry Modifications: Windows persistence techniques

Privilege Escalation

• Local Privilege Escalation: Exploit local vulnerabilities
• Domain Privilege Escalation: Active Directory attacks
• Kernel Exploits: Operating system vulnerabilities
• Misconfiguration Abuse: Weak permissions and settings

5. Analysis and Reporting

Evidence Collection

• Screenshots: Visual proof of successful exploitation
• Log Files: System and application logs
• Network Captures: Packet analysis and traffic flows
• Command Output: Results of executed commands

Risk Assessment

• CVSS Scoring: Common Vulnerability Scoring System
• Business Impact: Potential damage to organization
• Exploitability: Ease of exploitation
• Remediation Effort: Cost and complexity of fixes

OWASP Top 10 Testing

1. Injection Flaws

• SQL Injection: Database query manipulation
• NoSQL Injection: NoSQL database attacks
• LDAP Injection: Directory service attacks
• Command Injection: Operating system command execution

2. Broken Authentication

• Session Management: Session fixation, hijacking
• Password Security: Weak passwords, storage issues
• Multi-factor Authentication: Bypass techniques
• Account Lockout: Brute force protection testing

3. Sensitive Data Exposure

• Data in Transit: Unencrypted communications
• Data at Rest: Unencrypted storage
• Backup Security: Unsecured backup files
• Log Security: Sensitive information in logs

Tools and Frameworks

Network Testing

• Nmap: Network discovery and port scanning
• Masscan: High-speed port scanner
• Zmap: Internet-wide network scanner
• Unicornscan: Asynchronous network scanner

Web Application Testing

• Burp Suite: Comprehensive web application testing
• OWASP ZAP: Open-source web application scanner
• Nikto: Web server scanner
• Dirb/Dirbuster: Directory and file brute forcing

Exploitation Frameworks

• Metasploit: Comprehensive penetration testing framework
• Cobalt Strike: Advanced threat emulation platform
• Empire: PowerShell post-exploitation framework
• BeEF: Browser exploitation framework

Post-Exploitation

• Mimikatz: Windows credential extraction
• BloodHound: Active Directory attack path analysis
• PowerSploit: PowerShell post-exploitation toolkit
• LinEnum: Linux enumeration script

Reporting Best Practices

Executive Summary

• High-level Overview: Non-technical summary for management
• Risk Rating: Overall security posture assessment
• Key Findings: Most critical vulnerabilities
• Business Impact: Potential consequences of exploitation

Technical Details

• Vulnerability Descriptions: Detailed technical explanations
• Proof of Concept: Step-by-step exploitation procedures
• Evidence: Screenshots, logs, and command output
• CVSS Scores: Standardized vulnerability ratings

Remediation Recommendations

• Immediate Actions: Critical fixes requiring urgent attention
• Short-term Solutions: Fixes to implement within 30 days
• Long-term Improvements: Strategic security enhancements
• Compensating Controls: Temporary risk mitigation measures

Conclusion

Effective penetration testing requires a systematic approach, proper tooling, and comprehensive reporting. Regular testing helps organizations identify and address security weaknesses before they can be exploited by malicious actors.