The industry has been doing penetration tests (or pentests for short) for years now. It started as a bespoke, specialized activity to something that many organizations do on an annual basis at least. Couple that with the deluge of more continuous or ongoing security activities and it appears there’s a lot of coverage. Yet…the pressures on organizations from regulatory changes (CMMC, PCI-DSS, new HIPAA changes, etc.), customer requirements, and a continued evolution of threat actor tactics has only continued to grow.
There is a need for penetration testing to move from compliance exercise or fancy hacker firm escapades into a more strategic security function. As we navigate 2025, security leaders now face and must navigate a landscape of AI, cloud-native architectures, complex layers of suppliers, and regulation upon regulation.
The Compliance-Security Convergence
Historically, many organizations approached penetration testing as a checkbox exercise, primarily driven by compliance requirements. Today, the relationship between penetration testing and compliance has fundamentally changed—regulatory frameworks now demand more than superficial assessments conducted once or twice a year.
Modern frameworks like PCI DSS 4.0, NIST 800-53, and updated ISO 27001 standards have shifted toward continuous security validation models. The EU’s NIS2 directive emphasizes real-world attack simulations rather than static assessments. Healthcare compliance frameworks, such as HIPAA’s new proposed changes in response to escalating ransomware threats, favor threat-informed testing methodologies.
This regulatory evolution creates both challenges and opportunities for security leaders. The compliance-driven pentester of 2020 has given way to the strategic security validator of 2025—a professional who not only identifies vulnerabilities but also demonstrates resilience against realistic threats. This, in my opinion is a good thing. Thinking about it in reverse too, the output of a pentest should do more for security leaders to help them prepare for the necessary compliance work they must deal with.
Five Strategic Shifts Reshaping Penetration Testing
1. AI-Augmented Testing: From Discovery to Decision Support
Artificial intelligence is actively transforming how penetration tests are conducted, analyzed, and integrated into security programs. Unlike the rudimentary scanning tools of previous years, which were almost entirely deterministic, today’s AI-augmented platforms can adapt to what they observe. There’s also opportunity to do more than find vulnerabilities—rather to contextualize them within your environment.
The more sophisticated security teams we’ve spoken to are looking at and deploying AI-driven tools to:
- Simulate thousands of attack vectors simultaneously, learning from each attempt
- Identify patterns and relationships between vulnerabilities that human analysts might miss
- Prioritize remediation efforts based on actual exploitability rather than generic severity ratings
While automation handles the high-volume, repetitive aspects of testing, the critical human element remains essential for creative exploits and contextual analysis. The modern security leader recognizes that AI is a force multiplier for human expertise, not a replacement. This is especially true when talking about the way that a pentest connects to everything else in an organization.
2. Clouds, Containers, Functions, and SaaS: Testing What You Can’t Touch
As organizations continue pushing cloud-native and hybrid infrastructures, penetration testing methodologies have evolved to address these ephemeral, API-driven environments. Testing a modern cloud environment requires specialized knowledge of provider-specific attack surfaces, shared responsibility boundaries, and orchestration vulnerabilities.
Effective cloud penetration testing typically includes:
- Evaluating misconfigurations and over-privileged service accounts across multi-cloud environments (ranging from IaaS, PaaS, SaaS, and beyond)
- Assessing container security, from image vulnerabilities to orchestration weaknesses
- Evaluating serverless functions and infrastructure-as-code deployments for security flaws
For security leaders, this demands a shift in perspective—from network perimeter-based thinking to identity-based and data-oriented security models that accommodate cloud-native architectures. When selecting penetration testing partners, prioritize those with demonstrable expertise in your specific cloud ecosystem rather than general IT security credentials. Also be weary of getting relatively canned and fixed test scopes and approaches; effective strategy doesn’t come in a box and neither does an effective pentest.
3. The Up and Down of PTaaS: Transforming Delivery Models
The emergence of Penetration Testing as a Service (PTaaS) platforms was one of the most significant shifts in how security validation is delivered and consumed. It was very hot for some time and in my experience, hit the same inevitable ceiling that many bespoke security solutions do…nobody wants another dashboard to manage and review. The output should come and integrate with the environment as it is; conversations with hundreds of other CISO’s over the last few years confirmed this same dynamic.
So there’s now forks in the road with traditional project-based engagements, platforms providing on-demand testing, tangential tools doing continuous monitoring, and a push for integrated management of findings across the board. All of these trends are changing the economics and effectiveness of security testing and there’s less apples to apples comparisons to make.
Modern pentest deliver models deliver several strategic advantages:
- Subscription-based access to both automated testing tools and human expertise
- Continuous visibility into security posture through real-time dashboards and metrics
- Seamless integration with the way developers do their work
- Efficient retesting capabilities to validate remediation without the overhead of new engagements
The most effective pentest delivery today isn’t necessarily those wrapped up in a snazzy dashboard, it’s those that that balance automation with human expertise and a program-focus. Using technology to scale routine testing while leveraging creative, experienced pentesters for complex scenarios and bridge building to all the other moving pieces of a security program is key. This hybrid approach ensures both broad coverage and deep insights into not only critical vulnerabilities but risk.
4. Continuous Security Validation: Beyond Annual Assessments
Perhaps the most significant shift in penetration testing strategy is the move from point-in-time assessments to continuous security validation integrated with development and operational workflows. The tool support here has exploded across network, cloud, web, API, and all sorts of attack surface. Organizations embracing DevSecOps have transformed how frequently and thoroughly they test their environments.
Progressive security programs now implement:
- Layers of automated scanners that are regularly tuned to provide high-signal results
- Automated regression testing integrated into CI/CD pipelines
- Breach and attack simulation (BAS) tools that continuously validate security assumptions
This transition to continuous validation aligns security testing with the pace of modern software development and infrastructure changes. For security leaders, this means when you do engage penetration testers, your scope should compliment these many layers so you’re getting to the real risks and strategic opportunities.
5. Adversary Simulation: Testing What Matters
Traditional vulnerability scanning focuses on deterministically identifying technical weaknesses, but modern penetration testing increasingly embraces adversary simulation to validate entire security programs—not just technical controls. This approach tests detection, response, and resilience capabilities alongside vulnerability identification.
Leading security programs now incorporate:
- Red team operations that leverage tailored threat profiles to emulate specific threat actors targeting your industry
- Social engineering assessments that evaluate human vulnerabilities and the technical stacks and authN/authZ flows they interact with
- Purple team exercises that improve blue team detection and response capabilities
These methodologies, often mapped to frameworks like MITRE ATT&CK, provide security leaders with insights into how well their security investments would perform against actual threats—not just theoretical vulnerabilities.
Conclusion: From Compliance to Capability
This move, of penetration testing from compliance checkbox to strategic security function is a great opportunity for forward-thinking security leaders. There is a chance to leverage the compliance requirement to get so much more than we traditionally have. Part of this will be driven and dealt with by internal teams, part of it will be supported by cutting edge tools, and some of it will be executed by the third party partners who get it (the big picture that is).
The more successful security programs in 2025 will be those that take these hordes of compliance requirements and really break down the spirit of the controls and get strategic value out of each checkbox. For security leaders navigating this transition, the key is to plan up front with a more strategic focus, then select testing partners and methodologies that align with your specific threat landscape, technology environment, and business objectives. The goal isn’t just to pass the next audit but to build genuine resilience against the threats that matter most to your organization.
Ready to Transform Your Penetration Testing Approach?
Is your current penetration testing program delivering strategic value beyond compliance checkboxes?
At Sidekick Security, we specialize in helping security leaders evolve their security programs to the next level. Taking penetration testing from periodic assessments to strategic security functions is a part of that journey. Our team of former CISOs and security experts brings deep expertise in modern testing methodologies that align with both compliance requirements and real-world threats.
Schedule a Strategic Penetration Testing Consultation
During this complimentary 30-minute session, we’ll:
- Evaluate your current penetration testing approach against industry best practices
- Identify opportunities to enhance the strategic value of your testing program
- Provide recommendations tailored to your specific compliance requirements and threat landscape
- Explore how our flexible testing methodologies can complement your existing security initiatives
This thought leadership piece was developed by Sidekick Security, providing expert penetration testing and strategic security guidance for organizations navigating complex threat landscapes and regulatory requirements.