Is AI-augmented pentesting the solution to a future-proof cyber strategy? | OnSecurity

Collaborative, not Competitive: Is AI-augmented pentesting the solution to a future-proof cyber strategy?

Explore how AI augmentation is revolutionising penetration testing, blending automation with human expertise to enhance cybersecurity and stay ahead of emerging threats.

Daisy Dyson
Daisy Dyson
Junior Content Executive
March 28, 2025

In the blink of an eye, artificial intelligence and emerging technology are shattering the old rules of cybersecurity, rendering traditional penetration testing as obsolete as a horse-drawn carriage in the age of electric cars.

Periodic, manual security assessments are no longer sufficient. Today's attackers use sophisticated, automated methods to probe vulnerabilities with unprecedented speed, utilising emerging technologies to victimise and outwit poorly equipped organisations.

As businesses face increasingly complex networks and interconnected technologies, the battle against cyber threats demands a forward-looking strategy that anticipates current and imminent challenges.

In response, the cybersecurity industry is integrating artificial intelligence and human expertise to create more adaptive and intelligent security solutions.

This is not about replacing human skill, but amplifying it. The future of penetration testing lies in a powerful collaboration between AI-driven tools and the creativity of skilled security experts. But how exactly is AI and pentesting beginning to converge? And how can business owners stay ahead of this tidal wave of incoming change in the cybersecurity world?

The Current State of Pentesting

Penetration testing, or pentesting, traditionally involves a manual assessment of security measures to identify vulnerabilities.

Ranging from network penetration to web application assessments, penetration testing is an umbrella term used to encompass a broad range of technical approaches to assessing an organisation’s security posture to identify vulnerabilities before malicious hackers do.

However, with the rise of cloud computing, remote work, and the increasing adoption of IoT devices, the attack surface has grown significantly, making it far harder to effectively secure every potential entry point. Not only this, but the integration of intelligent technology into both work and home life has accelerated the evolution of cyber threats tenfold, with attackers becoming more sophisticated and resourceful every day.

These various components combined have rendered one-off pentests obsolete to organisations, prompting an influx of regular, scheduled testing.

In response to these challenges, pentesting has begun to lean more on automated tools and AI-driven solutions to speed up assessments and enhance efficiency. While these tools offer impactful support, human expertise remains vital for interpreting results and spotting vulnerabilities that automated systems might miss.

The Future of Pentesting: What’s Next?

AI and Machine Learning in Pentesting

The normalisation and widespread adoption of AI tools is likely nothing new to your organisation. Since OpenAI’s chat-transforming tool ChatGPT became publicly commercialised in 2022, competitors have rushed forward to offer increasingly intelligent alternatives, optimising everything from everyday queries to entire workflows.

It’s no surprise that the future of pentesting will be largely influenced by AI and machine learning. These technologies will help to identify vulnerabilities at scale and possibly even predict potential attack vectors based on patterns and trends.

With the need for continuous, real-time vulnerability assessments an increasing priority for security-conscious businesses, AI-augmented penetration testing will allow pentesting vendors to support clients continually, instead of waiting for periodic pentest engagements.

Increased Integration of Automation

Automation will play an increasingly important role in pentesting. While automation can’t replace the human element entirely, it can handle repetitive tasks such as scanning for known vulnerabilities or testing for common configuration errors. The combination of automation with skilled testers will streamline pentesting processes.

Continuous Pentesting and Red-Teaming

The future is heading towards continuous, on-demand pentesting, often in the form of ‘Red Teaming.’ Unlike traditional pentests, which may only happen a few times a year, continuous engagement will involve ongoing, simulated attacks on systems to mimic how adversaries would attack over time.

This is crucial in supporting organisations in staying ahead, as cyber threats become increasingly intelligent and automated.

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.

Widespread Adoption of 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.

How should leaders adapt for the future of offensive security?

The rapidity of change occurring in the cyber industry right now means only those who adapt to the evolving environment will benefit from enhanced security, greater operational efficiency, and a competitive edge in an increasingly digitised world.

The many new prospects presented by emerging technologies and cyber trends are set to revolutionise the pentesting game entirely, providing operational efficacy and fortitude against threats unlike anything business leaders have ever experienced.

Leaders looking to trailblaze their cybersecurity strategy in the coming year should:

Adopt Agile Security Models

Gone are the days of rigid and one-off pentesting. With the influx of flexible pentesting options and the capability of AI automations, it’s recommended that leaders take a more flexible and agile approach to security.

This means integrating pentesting into the development lifecycle through best practices. By embedding security from the start, organisations can identify issues early in the development process and mitigate risks before they become threats. The introduction of real-time, continuous testing capabilities will ultimately offer significant rewards to those who integrate security as an ongoing process, rather than treating it as an occasional, scheduled check-up.

Harness AI-Augmented Services

AI-augmented services blend AI technology’s capabilities with the skill and experience of human testers to enhance efficiency and speed up results. This innovative hybrid approach allows human pentesters to focus on the most critical areas while automating and expediting the simpler, more repetitive tasks through AI integration.

The result? A budget-friendly, accelerated method of pentesting that your cybersecurity strategy future-proofs your organisation from emerging threats. Leaders should view AI-augmented pentesting as a powerful defence against the growing threat of cyber attacks.

Prioritise Risk-Based Testing

Finite resources and budgeting mean companies should focus their pentesting efforts on high-risk assets, such as customer data, financial systems, and critical infrastructure. Leaders must adopt a risk-based approach to determine what needs to be tested and at what frequency.

Centralise and Coordinate Pentesting Efforts

With the growing use of multiple testing tools and the shift to continuous pentesting, leaders must centralise and coordinate efforts across teams. This could mean integrating pentesting results with incident response teams, operations, and development teams to ensure vulnerabilities are promptly addressed.

The Human Element: Why Pentesters Matter

The exciting possibilities of AI in no way render pentesters obsolete. The human element of pentesting, despite AI’s breadth of capabilities, remains an indispensable and non-negotiable part of achieving robust security.

AI can automate repetitive tasks, scan for known vulnerabilities, and process vast amounts of data quickly, but it still lacks the creativity and adaptability that skilled pentesters bring to the table. Pentesters can think like attackers, approaching systems from unconventional angles and identifying subtle weaknesses that AI tools might miss, built on years of experience and the unique human ability to aptly contextualise- and then effectively imitate- real-world scenarios.

Unlike AI, human testers can also interpret the business impact of vulnerabilities, providing actionable insights that align with an organisation's specific risk profile.

Every industry has its unique vulnerabilities, needs, and regulatory requirements, and this dynamic landscape is something only a human can fully understand and offer tailored recommendations for.

Furthermore, pentesters are vital in refining AI-driven tools by training them with real-world scenarios and complex attack vectors that go beyond scripted patterns.

Collaborative, not Competitive

As cyber threats evolve, the combination of AI and human expertise ensures a deeper, more thorough security assessment, making human pentesters an essential part of any modern security strategy. Leaders looking to future-proof their cybersecurity strategy should take an agile approach, acknowledging both the impressive potential of AI automation and the irreplaceable necessity of human skill and experience.

Together, AI-augmented penetration testing offers a forward-thinking approach to cyber-resilience, with human expertise complementing the efficacy of AI automations to generate powerful pentesting results.

Optimise your cybersecurity strategy and assert your organisation as a trailblazer in the competitive cyber space with OnSecurity’s revolutionary AI-augmented end-to-end penetration testing platform. Streamline your testing workflow and continuously monitor for vulnerabilities, allowing for rapid results and remediation. Find out more here.

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