From Risk to Resilience: A Healthcare Executive’s Guide to Cyber Insurance Success

By Darrell Keeling, Ph.D., SVP, IT & CISO, Parkview Health

Technology executives within healthcare organizations have witnessed firsthand how the conversation around cyber insurance has evolved from a back-office procurement exercise to a boardroom-level strategic priority. In 2025, securing cyber insurance is no longer as simple as filling out a renewal application and hoping for the best. Underwriters are asking more challenging questions, requiring greater transparency, and expecting more advanced security controls than ever before.

For those preparing for an upcoming renewal, the message is clear: what was considered a “strong” security posture just a few years ago is now viewed as the absolute minimum baseline. Organizations that fail to recognize this shift risk higher premiums, reduced coverage, or being declined altogether. The question then becomes: how can security leaders position their organizations for success in this new environment?

It starts with governance and compliance. Insurers want to see that organizations are not just compliant on paper but are actively managing and reviewing adherence to regulations like the General Data Protection Regulation (GDPR), the California Consumer Privacy Act/California Privacy Rights Act (CCPA/CPRA), the Health Insurance Portability and Accountability Act (HIPAA), and other state and federal cybersecurity regulations. This is especially critical in healthcare, where organizations handle sensitive patient data, including genomic and diagnostic information. Annual reviews of compliance programs are no longer a “nice-to-have”—they are expected.

Securing cyber insurance today isn’t about checking boxes, it’s about proving that your organization leads with accountability, resilience, and a clear strategy to manage emerging risks.

Employee awareness is another area that cannot be overlooked. Despite all the sophisticated tools available, human error remains the leading cause of security incidents. Leading organizations ensure staff undergo regular security and privacy training, including simulated phishing exercises and fraud prevention awareness. Insurers ask for evidence of these programs because they recognize that an informed workforce is one of the most effective first lines of defense.

Data protection is also under close scrutiny. During recent insurance renewals, organizations have been required to demonstrate how they secure data at rest and in transit, and how they segment it across their networks. Many have implemented zero trust principles and micro-segmentation to meet these rising expectations. If data environments are not properly segmented and access is not tightly controlled through role-based permissions, underwriters will likely present challenging questions.

From a technical controls perspective, the days of simply listing “antivirus and firewalls” as adequate protections are long gone. Insurers now expect to see Endpoint Detection and Response (EDR), Privileged Access Management (PAM), Domain Name System (DNS) filtering, and active vulnerability management programs. Multifactor Authentication (MFA) is no longer negotiable; it is a requirement across privileged accounts, remote access systems, and third-party integrations. Without enforcing MFA everywhere possible, organizations are not even at the starting line.

Insurers also place significant weight on monitoring and detection capabilities. One of the first questions asked is whether the organization has a Security Operations Center (SOC) and if it is staffed 24/7. Insurers want to know which Security Information and Event Management (SIEM) platform is used, how logs are retained and analyzed, and how quickly the organization can respond to an incident. Without a mature detection and response program, negotiating favorable coverage will be difficult.

Patching and vulnerability remediation remain top concerns. Delays in patching are one of the easiest ways for attackers to gain access. Leading organizations have formalized patch management policies with clear timelines for addressing critical, high, and medium vulnerabilities. They do not simply scan for vulnerabilities—they act on the results immediately and pay special attention to known exploitable through remediation. Insurers are now asking for proof of these practices.

Ransomware resilience has become its own area of scrutiny. Insurers expect organizations to demonstrate that their backups are encrypted, stored offsite or in air-gapped environments, and regularly tested for integrity. MFA is also implemented for backup environments, and quarterly recovery exercises are conducted. Insurers want to know that if an organization is hit with ransomware, it can recover quickly without paying a ransom. Without this capability, organizations should expect exclusions or higher premiums.

Another area of increased focus is financial controls—specifically around preventing wire fraud and Business Email Compromise (BEC). Leading organizations have implemented authorization processes for large fund transfers, requiring independent verification of any changes to vendor payment instructions. While these may seem like small steps, they are directly tied to reducing the risk of financial losses that insurers are increasingly reluctant to cover.

One of the most significant changes observed is the growing importance of AI governance. As organizations adopt AI and ML across clinical, financial, and operational functions, insurers require clear visibility into how associated risks are being managed. Insurers ask whether organizations have documented AI policies, whether agentic AI systems are treated like privileged users, and how outputs are monitored and validated to prevent data leakage or biased decision-making. These are no longer hypothetical concerns; they are now fundamental underwriting factors.

In healthcare, this scrutiny is even more intense. AI models handle sensitive genomic data, patient diagnostics, and claims decisions. Insurers want assurance that explicit patient consent is obtained where required and that AI tools are not unintentionally introducing privacy violations. Leading organizations are reviewing and piloting tools to inspect AI prompts and outputs before they create compliance or ethical issues. Additionally, these organizations ensure that humans remain in the loop for all processes, leveraging AI throughout the change management lifecycle. Without this oversight, organizations introduce risks that could jeopardize their ability to secure adequate insurance coverage.

Cyber insurance is no longer just about financial protection after a breach. It is now a comprehensive evaluation of how organizations govern data, manage emerging technologies, and lead through complex, evolving risks. Technology executives must actively participate in these discussions at the highest levels of their organizations. Leadership, transparency, and preparation will determine whether organizations secure the coverage they need—or find themselves exposed when it matters most.