Blending brains and bots: The critical role of experience in AI-assisted penetration testing

What is penetration testing

Penetration testing, or pen testing, is a proactive security measure where cyber security experts identify and exploit vulnerabilities within systems, networks, and applications that may not have been found otherwise. By uncovering and addressing these weaknesses, you can stay ahead of malicious actors and safeguard your organization, stopping attacks before they occur. In fact, penetration testing is becoming so common that they are being included in compliance requirements like PCI DSS 4.0.

The growing role of AI in penetration testing

AI is transforming cyber security. It processes vast amounts of data, recognizes patterns, automates repetitive tasks, and analyzes historical attack data to spot vulnerabilities. However, AI is only as effective as the researchers and models behind it. While AI scales up penetration testing, it still lacks the nuanced understanding that human experts provide. That’s why combining AI with human expertise is key.

Real world use cases

AI streamlines penetration testing, making it faster and more efficient in several ways:

• Code generation: Generative AI quickly creates scripts in different programming languages, speeding up the process.
• Cryptography: AI helps identify various types of algorithms and encode and decode of values.
• Data analysis and pattern recognition: Machine Learning (ML) spots patterns and anomalies in network traffic, system logs, and system behaviours, giving security professionals the insights they need to launch effective simulated attacks and pivot quickly during testing.
• Exploit development: Advanced AI tools suggest potential exploits based on the vulnerabilities they find.
• Social engineering and cyber threat intelligence: AI gathers open-source intelligence (OSINT) about your organization, executives, and staff, adding valuable context to reconnaissance efforts during attack simulations.

Achieving what AI alone can’t in offensive security today

Despite AI’s benefits, the experience and insights of seasoned penetration testers remain critical. Offensive security subject matter resources bring critical thinking, creativity, and contextual awareness that AI simply can’t replicate, such as:

• Business objectives and grasping context: Each business faces unique security challenges. Experienced testers ensure their assessments align with your business objectives and risk management strategies. For example, knowing the context –– like someone’s gender, can help guess the answer to a security questions.
• Customized attack simulations: Experienced testers develop bespoke attack simulations that mimic real-world threats incorporating advanced techniques.
• Strategic guidance: Testers can interpret results, transforming complex information into clear insights for decision-makers. Communicating findings in a manner that resonates with both technical teams and executive audiences.
• Building trust and cultivating connections: Trust is crucial in cybersecurity. Businesses rely on their security teams to safeguard sensitive information effectively. Seasoned testers not only build relationships with stakeholders but also foster a culture of security awareness across the organization.
• Critical thinking: Experienced professionals analyze the facts, and based on their expertise, situation, and objectives, make the correct decision on how to proceed in each case, providing greater accuracy in whole process. This is a clear advantage of an experienced offensive security professional over AI, which becomes more evident in scenarios, such as Web Application Penetration Testing, where understanding the application context and software developers’ thought processes can provide a human penetration tester an understanding of meaning of a particular code variable, flag, or cookie –– something that current AI tools lack an understanding of.

In conclusion

AI has revolutionized cyber security by enhancing efficiency and effectiveness in penetration testing assessments in areas like code generation, data analysis, encoding, and decoding. However, true innovation and deep security insights come from the collaboration between advanced AI tools and skilled human expertise –– as AI is only as good as the humans and data sets that train it.

To navigate the evolving threat landscape, your business needs a partner that understands how to blend technology with real-world experience to develop a comprehensive, adaptable security strategy. Reach out to our team of expert cyber security advisors to jumpstart your efforts today.