Security | Threat Detection | Cyberattacks | DevSecOps | Compliance

It’s become pretty standard to expect the help of AI with automating tasks, with penetration testing being no exception. As AI-driven tools grow more sophisticated, some have posed the question: could these systems render the traditional human pen tester obsolete entirely? We’ll explore the strengths and limitations of AI when it comes to offensive security and predict the role human red team expertise still has to play in an increasingly automated world.

AI penetration testing is changing how organizations identify and exploit vulnerabilities. Instead of relying on traditional manual tests or basic automated scans, autonomous systems now simulate attacker behavior continuously and at scale. These systems use agentic AI to execute real-world exploits, reduce noise, and shift security left, all while keeping human experts focused on the creative flaws machines can’t yet catch.

Federal Risk and Authorization Management Program (FedRAMP) penetration testing compliance is a formal and systematic assessment that all Cloud Service Providers (CSPs) must conduct before providing their services to the U.S. government to meet stringent security criteria. The hands-on test allows security professionals to emulate the techniques of malicious actors to determine whether they can bypass the system’s security measures.

FedRAMP has strict requirements for the security of the companies looking to earn their certification. Among the many requirements you need to navigate are tests from your C3PAO, simulating malicious actors and common threat vectors. In order to understand what you need to do to pass, it’s worth going over what penetration testing is, what red teaming is, what the scope of FedRAMP pen testing includes, and what the rules of engagement encompass.

Penetration testing (“pentesting”) has shifted from a once-a-year checkbox to a continuous necessity. In fact, by 2025 the pentesting industry is expected to hit $4.5 billion as companies race to find vulnerabilities before attackers do. Yet 38% of companies only run 1–2 pentests per year – leaving long gaps where new flaws can creep in. That’s a dangerous game when 73% of breaches involve exploiting web app vulnerabilities.

Managed Service Providers (MSPs) sit on the front line of cyber‑defence for thousands of small and midsize businesses. Yet many still hesitate to add penetration testing (pentesting) to their security stack, largely because of persistent myths—myths that are steadily being dismantled by real‑world breach data. Fresh breach evidence makes the cost of that hesitation impossible to ignore.

In January of this year, significant changes to the HIPAA Security Rule were proposed by the Office of Civil Rights for the Department of Health and Human Services (OCR). The proposed update to the HIPAA Security Rule, published on January 6, 2025, introduces a significant new requirement: all covered entities and business associates must conduct penetration testing of their electronic information systems at least once every 12 months.

The real risk in M&A isn’t hidden. It’s just inconvenient to surface. Everyone’s pushing for closure. Security gets boxed into a checklist, technical debt gets rebranded as “Post acquisition planning,” and the systems you’re about to inherit stay largely unchallenged until it’s too late.