Penetration Testing

Pen-testing is essential for various reasons:

• Identify vulnerabilities and weaknesses before attackers can exploit them
• Improve security posture by identifying and mitigating weaknesses by boosting defences
• Ensure compliance and meet regulatory and industry standards, such as GDPR, PCI DSS etc.
• Testing the efficacy of controls and systems currently in place to ensure a potential attack would be caught
• Improve risk management by understanding potential impacts and prioritising remediation.
• Demonstrate due diligence and proactivity to stakeholders, including customers and partners.

Pen-testing works systematically, moving through various key processes. This includes:

1. Planning and Reconnaissance:
   • Determine what systems and areas will be tested
   • Collect data about the target through public sources (based upon use case)
2. Scanning
   • Network Scanning: Use tools to identify open ports, services, and network vulnerabilities
   • Vulnerability Scanning: Analyse the target for known vulnerabilities using automated tools
3. Exploitation:
   • Simulate Attacks: Attempt to exploit identified vulnerabilities to gain unauthorised access
   • Multiple Techniques: Use various methods such as injecting malicious code, bypassing authentication, or exploiting software bugs
4. Post-Exploitation:
   • Assess impact, including  extent of access gained and the potential damage that could be caused
   • Document access levels achieved and data compromised to demonstrate the impact
5. Reporting:
   • Provide a comprehensive report detailing the vulnerabilities found, exploitation methods used and the potential impact
   • Actionable recommendations for mitigating identified vulnerabilities and issues, to improve the overall security

The steps above may seem straightforward, a good pen-tester will be able to understand how to leverage multiple different (potentially low level) findings to achieve part of a larger objective.

When planning a pen-test, several critical factors must be considered to ensure the test is effective, comprehensive, and aligns with the organisation’s goals and regulatory requirements. Here are key considerations:

1. Define Objectives and Scope
   • Identify what you aim to achieve (e.g. identifying vulnerabilities, testing incident response)
   • Determine which systems, networks, applications, and data will be included or excluded from the test
2. Type of Test
   • Black Box: Testers have no prior knowledge of the system
   • White Box: Testers have full knowledge, including access to architecture and source code
   • Gray Box: Testers have partial knowledge of the system
3. Compliance and Legal Considerations
   • Ensure the test meets industry standards and regulatory requirements (e.g. GDPR, PCI DSS)
   • Obtain necessary approvals and legal clearances to avoid unauthorised access issues
4. Choosing the Right Team
   • Qualifications: Ensure testers have relevant certifications and experience (e.g. CEH, OSCP)
   • Trusted and Communicative: Ensure testers are reliable, trustworthy and clear, coherent communicators
5. Risk Management
   • Impact Analysis: Assess potential risks and impacts of the test on live systems
   • Contingency Plans: Develop plans to mitigate any adverse effects during testing
6. Communication and Coordination
   • Keep key stakeholders informed about the test plan, schedule, and objectives
   • Depending on the objective, inform relevant teams about the test to avoid false alarms and ensure cooperation
7. Methodology and Tools:
   • Testing Methods: Decide on the methodologies (e.g., network scanning, social engineering, application testing)
   • Tools and Techniques: Choose appropriate tools for vulnerability scanning, exploitation, and reporting
8. Timing and Schedule
   • Define the timeframe for the test, including start and end dates
9. Post-Test Activities
   • Remediation: Develop a plan to address identified vulnerabilities
   • Re-testing: Schedule follow-up tests to ensure vulnerabilities have been effectively mitigated;
   • Review and Feedback: Conduct a review meeting to discuss findings, lessons learned, and areas for improvement
10. Budget and Resources:
    • Allocate budget for the pen-test, including any tools and external expertise
    • Ensure the availability of necessary resources (e.g., personnel, technology) to support the testing process

By considering these factors, you can ensure that your pen-testing is well-planned, effectively executed, and provides valuable insights to enhance your organisation’s cybersecurity posture.