Penetration testing (also known as “pentesting”) are security assessments that simulate real attacks against systems, networks or applications to identify vulnerabilities and evaluate the effectiveness of implemented security measures.

What is Penetration Testing?

Penetration testing are proactive security assessments that:

  • Simulate real attacks against the organization’s infrastructure
  • Identify vulnerabilities before they are exploited by attackers
  • Evaluate the effectiveness of existing security measures
  • Provide recommendations to improve security posture

Penetration Testing Types

1. Black Box Testing

  • No prior knowledge of the target system
  • Simulate the perspective of an external attacker
  • Evaluate external attack surface of external attack surface

2. Gray Box Testing

  • Limited knowledge of the target system
  • Simulate attacks from malicious internal users
  • Balance between black box and white box

3. White Box Testing

  • Complete knowledge of the target system
  • Exhaustive analysis of code and configuration
  • Specific vulnerability identification of specific vulnerabilities

Penetration Testing Methodologies

OWASP Testing Guide

  • Web application focus on web applications
  • Structured methodology for web testing
  • Complete coverage of web vulnerabilities

PTES (Penetration Testing Execution Standard)

  • Standard methodology for penetration testing
  • Seven well-defined phases of seven well-defined phases
  • Applicable to any type of infrastructure

NIST SP 800-115

  • NIST technical guide for security testing
  • US federal methodology of US federal methodology
  • Focus on critical infrastructure

Penetration Testing Phases

1. Planning and Reconnaissance

  • Scope and objective definition of scope and objectives
  • Information gathering about the target
  • Attack vector identification of potential attack vectors

2. Scanning and Enumeration

  • Active service identification of active services
  • Open port detection of open ports
  • User and resource enumeration of users and resources

3. Vulnerability Analysis

  • Known vulnerability identification of known vulnerabilities
  • Insecure configuration analysis of insecure configurations
  • Patch and update evaluation of patches and updates

4. Exploitation

  • Vulnerability exploitation attempt of vulnerability exploitation attempts
  • Privilege escalation when possible
  • Successful attack vector documentation of successful attack vectors

5. Post-exploitation

  • Vulnerability impact evaluation of vulnerability impact
  • Attack propagation analysis of attack propagation
  • Accessible sensitive data identification of accessible sensitive data

6. Reporting and Recommendations

  • Detailed findings documentation of detailed findings
  • Vulnerability classification by severity
  • Specific remediation recommendations for remediation

Penetration Testing Tools

Reconnaissance Tools

  • Nmap: Port and service scanning
  • Recon-ng: Reconnaissance framework
  • theHarvester: Information gathering

Vulnerability Analysis Tools

  • Nessus: Vulnerability scanner
  • OpenVAS: Open source vulnerability scanner
  • Qualys: Cloud vulnerability scanner

Exploitation Tools

  • Metasploit: Exploitation framework
  • Burp Suite: Web application testing
  • OWASP ZAP: Web security proxy

Penetration Testing Benefits

Proactive Identification

  • Early detection of vulnerabilities
  • Security breach prevention of security breaches
  • Successful attack risk reduction of successful attack risk

Regulatory Compliance

  • Regulatory requirement satisfaction of regulatory requirements
  • Due diligence demonstration of due diligence
  • Standard compliance such as PCI DSS, HIPAA

Continuous Improvement

  • Regular security posture evaluation of security posture
  • Vulnerability trend identification of vulnerability trends
  • Security resource optimization of security resources

Important Considerations

Scope and Authorization

  • Clear definition of test scope
  • Formal authorization by the organization
  • Limit and restriction documentation of limits and restrictions

Operational Impact

  • Service interruption minimization of service interruptions
  • Coordination with operations teams
  • Maintenance window planning of maintenance windows

Confidentiality

  • Sensitive information protection of discovered sensitive information
  • Secure test data handling of test data
  • Secure temporary data destruction of temporary data

Professional Certifications

Technical Certifications

  • CEH (Certified Ethical Hacker): EC-Council
  • OSCP (Offensive Security Certified Professional): Offensive Security
  • GPEN (GIAC Penetration Tester): SANS

Advanced Certifications

  • OSEP (Offensive Security Experienced Penetration Tester): Offensive Security
  • GXPN (GIAC Exploit Researcher and Advanced Penetration Tester): SANS
  • CISSP (Certified Information Systems Security Professional): (ISC)²

Best Practices

Adequate Planning

  • Clear definition of objectives and scope
  • Appropriate methodology selection of methodology
  • Sufficient resource and time allocation of resources and time

Professional Execution

  • Strict methodology adherence of methodologies
  • Detailed documentation of all steps
  • Responsible sensitive information handling of sensitive information

Follow-up and Improvement

  • Recommendation implementation of recommendations
  • Applied correction verification of applied corrections
  • Regular test scheduling of regular tests