Day 9 – 12 Days of Unscripted with SST

Cyber Insurance

For Day 9, we revisit Episode Nine of Unscripted with SST, where Beau Elston joined us to clarify one of the most misunderstood parts of modern risk management: cyber insurance. Many business leaders believe that having a policy means they are protected, but in reality, cyber insurance only works when your organization fulfills every requirement specified in the policy. This episode examined how cyber insurance has evolved from a rare specialty coverage to a vital safeguard for SMBs, especially as ransomware attacks, business email compromise, and data breaches continue to increase. We discussed why insurers are paying closer attention, why claims are being denied more often, and how coverage gaps can reveal deeper IT and security issues.

Beau explained the biggest misunderstandings companies have about cyber insurance. Many believe they are covered, only to discover during an incident that they lack MFA, EDR, backup validation, or proper documentation, all of which can void a claim. Insurers are no longer just issuing policies; they are conducting assessments, security scans, and documentation reviews before underwriting or renewing coverage. Organizations that do not meet baseline security standards face higher premiums, limited coverage, or outright rejection.

A key theme of the episode was how proactive IT directly influences cyber insurability. Proactive IT goes beyond just security; it establishes the operational maturity that insurers seek, reduces risk, and helps companies meet policy requirements before applying. We also introduced CyberCheck, SST’s measurable scoring system that aligns with CIS Controls, Microsoft Secure Score, and insurer expectations. CyberCheck provides businesses with a clear view of their strengths, gaps, and overall readiness for both coverage and cyber risk.

The main message from Episode Nine was straightforward. Cyber insurance isn’t a safety net you turn to after an incident. It’s a partnership that needs preparation, operational discipline, and proactive IT controls. If your business hasn’t reviewed its insurance stance in the past year, now is the time. Cyber insurance only covers you if you can show that your environment was secure before the incident.