Rapid change has always been expected in cybersecurity. But the pace of transformation we’re witnessing today is unprecedented. In the past 12 months alone, UK businesses have experienced approximately 7.78 million cybercrimes of all types.* This staggering figure underscores a critical reality: as businesses face increasingly complex networks and interconnected technologies, the battle against cyber threats demands a forward-looking strategy that anticipates both current and imminent challenges.
AI is reshaping the cybersecurity landscape, and penetration testing is no exception. The way we assess, harden and continuously validate an organisation’s defences is evolving at breakneck speed. For many of us working in the field, this transformation is not only welcome but long overdue.
A Turning Point for the Industry
Historically, penetration testing, also known as pentesting, has relied on manual assessments to uncover security weaknesses. These evaluations were typically one-off exercises, limited in scope, with findings delivered days or even weeks after the testing. But while defenders waited for scheduled tests, attackers moved on. Today’s adversaries do not follow calendars. They automate, adapt quickly and exploit opportunities whenever they arise.
This is where AI is making a real difference, not by removing the human element, but by enhancing it.
Moving Beyond the Annual Test
One of the most significant shifts we are seeing is the move from periodic testing to continuous assessment. Businesses cannot afford to wait months between tests to discover they are exposed.
With AI-enhanced platforms, organisations gain real-time insights, allowing them to stay ahead of threats. Continuous testing not only identifies vulnerabilities early but also validates fixes and supports a more adaptive security posture. Combined with automated reporting and smart prioritisation, it delivers focused, actionable insights, reducing noise and helping teams respond more effectively.
The Rise of Pentesting as a Service (PTaaS)
Another prominent trend is the rise of PTaaS, where businesses can access pentesting services on demand through subscription-based models. This service offers flexibility, scalability and a way to make pentesting more accessible for organisations seeking to improve their security posture. This shift is particularly significant given that, in 2024, only 8% of organisations in the UK had conducted penetration testing, highlighting a major gap in proactive security practices that PTaaS aims to address.**
Adapting Pentesting for Cloud and Hybrid Environments
As more organisations migrate to cloud data storage, pentesting practices must evolve to cover cloud infrastructures. The future will see the integration of cloud-specific testing tools, and pentesters will need to gain expertise in hybrid environments to address vulnerabilities across on-premise and cloud systems. In fact, by 2024, 43% of organisations were operating in hybrid environments, highlighting the growing need for pentesting strategies that span both cloud and traditional infrastructure.***
Why Human Pentesters Still Matter
Even in a world of AI-powered tools, human expertise is essential. No system, however advanced, can replicate the intuition, curiosity, and critical thinking that experienced security professionals bring. The ability to think like an attacker, identify obscure flaws, and understand the business context of a vulnerability remains uniquely human.
AI can recognise patterns, but people can interpret nuance. AI can identify known issues, but humans find the unknowns. When it comes to offering strategic, tailored advice that fits a company’s risk appetite and operational reality, skilled practitioners remain the best option.
Human pentesters also play a crucial role in training and refining AI tools. They feed real-world insights into these systems, helping them understand complex attack vectors that go far beyond scripted logic.
The demand for such skilled professionals is evident following the UK government’s new £187m TechFirst scheme, designed to address the technical skills gap affecting 30% of cyber firms.
How Should Leaders Adapt for the Future of Offensive Security
- Adopt Agile Security Models: Static, one-off security checks are no longer enough. Embedding pentesting into the development lifecycle allows organisations to catch vulnerabilities early and continuously improve their security posture.
- Harness AI-Augmented Services: Combining AI with human expertise accelerates testing, reduces costs, and improves coverage. While AI handles repetitive tasks, human testers focus on complex problems, resulting in faster, smarter, and more effective outcomes.
- Prioritise Risk-Based Testing: Not all assets carry equal risk. Directing efforts towards high-value targets, such as customer data or financial systems, ensures resources are used where they matter most. A risk-based approach leads to more strategic and impactful testing.
- Centralise and Coordinate Pentesting Efforts: As testing becomes more continuous and automated, coordination is key. Centralising efforts across development, security, and operations teams ensures findings are actioned quickly and efficiently, closing vulnerabilities before they can be exploited.
The integration of AI into penetration testing is not a gimmick; it is a necessary evolution. It reflects a wider shift in cybersecurity towards more proactive, intelligent strategies.
Looking forward, I believe the most effective security models will be those that embrace flexibility, intelligence, automation, and human collaboration. This applies both within organisations and between people and the technologies they use.
