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Cyber Insurance Review & Due Diligence: Build the Paper Trail That Gets Claims Paid

If you’re a CEO, CISO, or CFO, the cyber market’s new reality is simple: underwriters price on evidence, not promises. Carriers now verify whether controls were implemented and operating, especially MFA, EDR, backups/restore, centralized logging, and IR/PAM. Our service aligns your environment to those expectations and assembles the insurer-ready evidence you’ll need at renewal or after an incident.


Why claims get challenged (and sometimes denied)

  • Controls not actually in place (or only partly): Some policies include a “minimum required practices” condition. When carriers investigate and find gaps versus what was represented on the application, they may deny the claim or seek rescission. The Columbia Casualty v. Cottage Health dispute is a well-known example where the insurer pointed to a “failure to follow minimum required practices” endorsement to avoid coverage. The case moved out of court to ADR, but it’s a cautionary tale: insurers will leverage these conditions when controls aren’t maintained. TechnethicsAdvisen Ltd.Inside Privacy

  • MFA misrepresentation: In 2022, Travelers asked a federal court to rescind a cyber policy after alleging the insured misrepresented its use of multi-factor authentication, a condition for coverage. Whether or not a court ultimately agrees, the filing shows carriers are willing to contest coverage when MFA is missing or mis-stated. Insurance JournalWilson Elser

  • Policy exclusions (e.g., “act of war”): The Mondelez v. Zurich clash over the NotPetya attack highlights how broad exclusions can be invoked to deny claims; that matter ultimately settled without precedent, underscoring how unsettled (and risky) the landscape can be. Clear due diligence and precise documentation won’t rewrite exclusions, but they can narrow disputes about whether you met your obligations. CSO OnlineReinsuranceNe.wsCybersecurity Dive

Bottom line: when controls or representations don’t match reality, you invite coverage fights at exactly the worst time.
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What we deliver

1) Align controls to carrier requirements

We test alignment for the controls that matter most to underwriters, MFA, EDR, backups/restore, centralized logging/retention, IR/PAM, and note any partials or gaps. You’ll see exactly what satisfies the carrier using tools you already own (turning on features before buying new ones).

2) Assemble an insurer-ready evidence packet (time-stamped)

We package exports, screenshots, backup restore logs, admin/audit logs, EDR/MFA coverage reports, and tabletop minutes into a clean, cross-referenced bundle. Every artifact is dated and attributable, so you can demonstrate controls were in place and operating.

3) Licensed agent/broker review

A state-licensed insurance agent or your broker reviews the packet for underwriting fit, flags premium-impact gaps and potential exclusions, and contributes a short memo to strengthen your negotiating position.

Proof: Most clients have an insurer packet ready in ~6 weeks, reducing back-and-forth and cutting renewal surprises.


What CEOs, CISOs, and CFOs gain

  • CEO: A defensible story you can take to the board: we did the work, we can prove it, and we’re prepared for scrutiny.

  • CISO: Less ambiguity and fewer disputes, one place with current, carrier-aligned proof of MFA, EDR, logging, backups/restore, and IR/PAM.

  • CFO: Predictable renewals and a clearer picture of exclusions vs. cost, with documented steps that protect the balance sheet.


Real-world failure patterns (and how we prevent them)

  1. “MFA everywhere” wasn’t actually everywhere. Carriers now verify enforcement on admins, users, and service accounts. Our packet includes MFA coverage reports and conditional access screenshots so there’s no ambiguity, plus a short gap/exception register tied to a timeline. The Travelers/ICS filing shows how quickly MFA gaps can become a coverage dispute. Insurance Journal

  2. “Minimum practices” promised, but not maintained. Policy endorsements can require you to continuously follow stated security practices. We map your practices to those commitments and include time-stamped proof so you’re not arguing after the fact. The Cottage Health matter demonstrates why this rigor matters. Technethics

  3. Backups existed, but restore proof was missing. After a ransomware event, adjusters may ask for restore evidence and retention settings. We include recent restore logs and architecture notes to show your capability, not just your intent. (Exclusions still apply; evidence reduces avoidable disputes.) SecureAuth


What’s inside the Insurer Packet (example table of contents)

  1. Cover letter & environment summary

  2. Control matrix (carrier requirement → tool(s) → evidence → status)

  3. MFA/IdP: policy exports, enforcement coverage, PIM/elevation controls

  4. EDR/XDR: deployment %, tamper protection, 30/90-day detection stats

  5. Backups/Restore: restore logs, retention settings, architecture summary

  6. Logging/SIEM: sources onboarded, retention, admin audit logs, sample queries

  7. IR/PAM: IR plan, tabletop minutes, privileged access workflows/logs

  8. Exceptions & compensating controls (with timelines)

  9. Licensed agent/broker memo (underwriting observations)


How we run it (fast cadence)

  • Week 1: Policy/binder & application intake, tool/evidence request, kickoff

  • Weeks 2–3: Control alignment checks, evidence collection, packet drafting

  • Week 4–5: Licensed agent/broker review; updates and clarifications

  • Week 6: Final packet + executive readout (and renewal prep calendar)


Start now: 5 artifacts your carrier will likely ask for

  • MFA enforcement & coverage (users, admins, service accounts)

  • EDR deployment & policy (coverage %, tamper protection, response workflows)

  • Backup/restore proof (recent restore log + retention)

  • Logging/retention (source list, retention policy, admin audit logs)

  • IR/tabletop (current plan, roles, tabletop agenda/minutes)


Have gaps? We’ll show how to close them with what you already own—and document the rest so your renewal is faster and your post-incident claim is stronger. Get in touch with Hire A Cyber Pro now at contact@hireacyberpro.com or book a call at your convenience https://www.hireacyberpro.com/book-online (We're not your lawyers; coverage always depends on policy terms and carrier decisions. Our goal is to maximize preparedness and defensibility.)


 
 
 

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