In a striking shift in enterprise cybersecurity, a majority of U.S. businesses are now shaping their defense strategies to meet cyber insurance compliance. According to Pentera‘s 2025 State of Pentesting report, 59% of surveyed enterprises implemented new security solutions specifically at the request of their insurance providers. This trend sees insurers now acting not just as backstops after a cybersecurity breach but as active stakeholders in pre-breach prevention.
From Passive Policies to Proactive Prescriptions
Cyber insurance providers have moved from reactive roles to becoming compliance enforcers. These firms now influence what tools companies deploy. In fact, 93% of CISOs reported receiving either a recommendation or a requirement from their insurers to adopt specific cybersecurity technologies.
With premiums stabilizing after years of increases, this insurer-driven approach suggests a maturing marketplace where risk mitigation is being frontloaded.
Pentesting Becomes Strategic and Insurer-Mandated
Pentesting, once primarily a checkbox exercise, has evolved as a way to measure cybersecurity. It now represents a strategic pillar of enterprise risk management. Nearly one-third of respondents cite cyber insurance requirements as a key reason for conducting penetration testing. This places it on par with regulatory compliance and impact assessments regarding insurer compliance mandates.
Security leaders are no longer testing to “prove compliance.” They’re testing because their insurers and their bottom line demand it.
Software-Based Pentesting Gains the Insurance Industry’s Trust
Historically seen as risky, software-driven penetration testing has quickly gained ground. Over half (55%) of enterprises now conduct in-house software-based pentesting. Fifty percent of CISOs rank it as their top method for exposing security gaps.
With rapid infrastructure changes occurring quarterly in 96% of enterprises, automation helps bridge the gap between dynamic environments and lagging validation practices. This trend directly supports insurers’ calls for more frequent and scalable assessments.
Budgets Align with Cyber Insurance Requirements
U.S. enterprises now spend an average of $187,000 annually on pentesting, over 10% of their IT security budgets. Notably, 50% of CISOs plan to increase pentesting investments in 2025. The driving force? Beyond regulation or executive mandates, many cited cyber insurance requirements as primary motivators.
This pivot reflects a broader transformation: pentesting is not just about defense but also about demonstrating readiness to those footing the bill for potential breaches.
Pentera’s View: Insurers Are Reshaping Cyber Risk
Jason Mar-Tang, Field CISO at Pentera, emphasized that “the pace of change in enterprise environments has made traditional testing methods unsustainable.” As companies reshape their security strategies, insurers have become key catalysts, pushing for automation and continuous validation.
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