Amid the technological advancements of 2025, CISOs are encountering increasingly complex security environments, facing heightened pressure to manage these challenges efficiently. With regulatory changes, widespread AI integrations into the workplace, and limited resources all posing both major complexities and constraints, it’s no surprise that many forward-thinking CISOs have already recognised the limitations of traditional periodic pentesting, and have instead begun to invest in AI-augmented testing services as a more continuous security solution.
But what exactly is meant by “AI-augmented” or automated penetration testing, and how can this help CISOs stay ahead of the game?
This blog will investigate some of the main challenges information security professionals face today, and how AI-augmented pentesting is changing old testing methods to offer a more effective and future-ready solution to these problems.
Current CISO challenges
Resource constraints
Resource constraints remain a major challenge for businesses of all sizes. Limited cybersecurity budgets often result in small internal security teams with stretched capacity, causing competing priorities left unaddressed.
While a pentest can be great for highlighting weaknesses and providing guidance and insight into an organisation’s security posture, the remediation efforts still ultimately fall on the shoulders of the security team. Stretched thin over patching, incident response, and compliance audits, it’s no wonder many cybersecurity professionals feel they are treading water.
Limited testing frequency
Traditional pentesting also limits the frequency of security assessments, with many organisations unable to afford frequent traditional tests due to budget constraints. Between these long periods, it’s more than possible that hackers may have infiltrated your networks, damaging your systems, exploiting sensitive information, and leaving your organisation vulnerable to further attacks.
Critical systems can evolve faster than testing cycles. By the time your annual pentest rolls around again, threat actors may have already traded company secrets on the dark web or installed ransomware without you being aware.
Expanding attack surfaces
Expanding attack surfaces caused by the increase of remote working, cloud migration, and SaaS applications have increased the complexity for IT leaders to manage. More endpoints mean more potential vulnerabilities for businesses, and, in turn, the security expertise needed to address vulnerabilities like these is stretched thin.
Compliance and regulatory pressures
As technology evolves, so does the need for rigorous security frameworks. CISOs face mounting compliance pressures from GDPR, SOC 2, ISO 27001, and PCI DSS, requiring fast, reliable assessment. Traditional periodic testing’s slow cycles can delay the ability to provide proof of compliance, creating additional challenges for already-stretched security teams and possibly leading to operational disruptions and loss of customer trust.
Talent shortages and skills gaps
Cybersecurity is facing a huge talent shortage- globally, there are millions of unfilled cybersecurity positions and not enough individuals with the relevant skillset to fill these spaces. Due to this, there has been an increasing reliance on AI-driven platforms to supplement human teams and tackle low-level, enumeration-based work.
Data overload and prioritisation challenges
Penetration tests often generate an overwhelming volume of findings, making it difficult for security teams to prioritise remediation effectively. This data overload can lead to critical vulnerabilities being overlooked or delayed in addressing. AI-driven risk scoring offers a powerful solution by analysing and prioritising vulnerabilities based on their potential impact and exploitability. This enables CISOs and security teams to focus their efforts on the highest-risk issues first, enhancing overall security and resource efficiency.
How AI is changing the penetration testing game
AI-augmented penetration testing transforms security validation by automating repetitive tasks like reconnaissance and vulnerability scanning, freeing human experts to tackle sophisticated business logic flaws requiring creative thinking.
For overworked CISOs, this delivers faster, more comprehensive assessments: automated systems continuously probe networks at machine speed, work that would traditionally consume days.
These tools prioritise high-risk assets, directing human skills where they matter most: finding organisation-specific weaknesses that automated systems cannot detect alone. AI-enabled reporting provides audit-ready, real-time insights, keeping organisations continually and proactively compliant rather than scrambling to book quarterly tests at the last minute.
Let’s break down the specific ways in which AI-augmented penetration testing supports
Continuous security assurance
Automated tools and AI-augmented pentesting from third-party vendors can reduce manual pressure placed on internal teams by providing more rapid, continuous security assurance than traditional periodic penetration testing.
This way, businesses can remediate vulnerabilities in real-time rather than waiting weeks or months between assessment cycles, while freeing up skilled internal security professionals to focus on complex threats and strategic security initiatives that require human expertise and judgment. Reducing the gap between traditional testing cycles increases the effectiveness of your security strategy, identifying vulnerabilities more quickly and minimising the risk window.
Intelligent prioritisation and fewer false positives
AI vulnerability scanning can analyse and score vulnerabilities present within your infrastructure based on risk, exploitability, and business impact. Following algorithmic information, the AI will review your networks for indications of unauthorised access, looking for any anomalous behaviour that could be an indicator that an attacker has breached the external or internal network.
It will take into account multi-factor authentication attempts, any triggered time-outs after a user repeatedly fails to give a correct password, and unusual network traffic to map out vulnerabilities where hackers could gain unauthorised access.
AI also triggers fewer false positives than static scanners alone, saving human time spent exploring illegitimate threats. This provides a more continuous outlook of your security posture than pentesting alone, keeping you proactive against threats. Learn more about penetration testing versus vulnerability scanning here.
AI vulnerability scanning greatly benefits CISOs and security teams by enabling them to focus remediation efforts on the most critical areas, reducing the risk window, and allowing normal operations to continue uninterrupted. By delivering precise insights into where additional cybersecurity focus is required, organisations save time, reduce costs, and efficiently distribute valuable human labour resources.
Enhanced reporting and insights
AI-driven penetration testing delivers audit-ready reports tailored for compliance and executive review. It offers predictive insights into emerging threats and attack paths, reducing false positives compared to traditional scanners. Using this advanced reporting, CISOs and security teams can effectively and punctually make informed decisions, enhancing their overall risk management.
Reducing manual workload
AI-augmented testing significantly reduces manual workload within a penetration testing company by taking care of low-level, repetitive tasks. This way, team efficiency and coverage are improved without requiring additional headcount, meaning more cost-efficient, rapid testing.
Human pentesters are therefore freed up to channel their expertise into more advanced work, including business-logic challenges, critical threats, and emerging attack vectors that require creative problem-solving. Combined, low-level AI support and high-level human threat identification provide 360-degree oversight of your threat landscape- far more thorough than manual testing alone.
Stay one step ahead of evolving threats and gain confidence in your security strategy with OnSecurity’s AI-augmented penetration testing services, designed to empower clients with continuous security insights through our consultative, platform-based approach. Get an instant quote here today.
