CYBER INSURANCE READINESS REVIEW
Cyber Insurance Readiness Review:
Stop Guessing on Your Application.
Someone in your organization made material representations about which security controls are in place, and those answers can affect whether the policy responds after a claim.
WHAT THIS PROTECTS
A Policy That Pays Is the Only Policy Worth Buying.
Cyber insurance only works if the claim survives the carrier’s investigation. This review gives leadership 3 things most organizations don’t have until it’s too late.
- You sign attestations you can stand behind, because every answer has been independently verified against your actual environment.
- You find the gaps before renewal, when they’re fixable, instead of after a breach, when they’re grounds for denial.
- You hold a claim position that survives forensic review, with documentation showing your controls were real, enforced, and in place.
THE ATTESTATION GAP
Why Cyber Insurance Claims Get Denied.
When your organization applied for cyber insurance, someone answered a questionnaire. Is MFA enforced on all accounts? Are backups tested? Is endpoint detection deployed on every device? The questions may vary by provider, but the weight of the answers do not. Someone checked yes, signed it, and the policy was issued on those answers.
After a breach, the carrier’s forensic team compares what you attested to against what was actually deployed. A material gap between what was represented and what was actually deployed can give the carrier grounds to dispute coverage or seek rescission, even when leadership believed the original answer was accurate.
This is settled practice, not theory. In Travelers v. International Control Services, Travelers alleged after a ransomware incident that MFA had not been deployed as represented on the application. Travelers sought rescission, and ICS ultimately agreed to a judgment rescinding the policy.
Here’s the part that should concern every executive who signs one of these applications. The person signing, has no independent way to verify the answers. IT said yes, so the answer was yes. That’s the gap this review closes.
I wrote a full Strategic Briefing on how these denials happen and what carriers actually check. Briefing #11
FIXED SCOPE
What a Cyber Insurance Readiness Review Covers.
I verify the controls carriers check most aggressively after an incident, assessed against CIS Controls IG1 and IG2 and mapped to the exact wording on your application and policy.
MFA enforcement scope. Every account and every access path, including remote access, admin accounts, and legacy logins. Carriers deny claims over a single unprotected path.
Endpoint detection and response. Verified coverage on workstations and servers by report, not by assumption.
Backup integrity. Whether backups are isolated from production, whether a restore has actually been tested, and whether you can prove both.
Incident response readiness. Cyber policies commonly require prompt notification, and some contain specific reporting windows or require the use of approved response providers.
Email security. Business email compromise remains one of the most common and most disputed claim types.
Security awareness training. Documented, current, and provable, since carriers increasingly ask for completion records rather than a yes.
Then I walk your application line by line and confirm each answer is true and enforceable, not aspirational.
TWO TIERS
Scoped to What Your Renewal Actually Requires.
Readiness Review Starts at $2,500
Independent Assessment and Findings Report
A focused assessment comparing your current environment against the controls your policy and application require. You receive a findings report with every gap prioritized by claim-denial risk, so you know exactly what needs to be addressed and in what order. What you do with the findings is up to you. Some clients hand the report directly to their MSP or internal IT to remediate.
This tier is right for you if:
- Your renewal is approaching and nobody has independently verified your answers
- You have an MSP or internal IT handling operations and need a second set of eyes on their work
- You want a independent audit done before the application gets signed, not after a claim gets filed
This engagement provides technical and operational readiness analysis, not legal advice, insurance placement or a guarantee of coverage.
Readiness Engagement Starts at $4,500
Full Assessment, Response Plan and Documentation Package. Scoped to your environment.
Everything in the Readiness Review, plus three additional deliverables carriers increasingly expect. You receive an incident cost exposure estimate prepared to support a coverage discussion with your broker. It considers recovery costs, business interruption, legal fees, regulatory notification and other likely incident expenses. I also develop a documented Incident Response Plan with named roles and a defined notification sequence, along with a documentation package covering each reviewed control, its scope, timestamps and verification records.
Technical remediation is performed by your internal IT team or MSP unless separately scoped. I provide remediation direction, coordinate the response when included in scope, and verify that completed corrections satisfy the application requirement.
This tier is right for you if:
- You want the gaps closed and documented, not just identified
- Your carrier or broker has asked for an incident response plan you don’t have
- You want an estimated incident cost range to support a more informed coverage discussion with your broker.
This engagement provides technical and operational readiness analysis, not legal advice, insurance placement or a guarantee of coverage.
THE DELIVERABLE
A Report Your Broker Can Actually Use.
Every engagement ends with a written report that tells you exactly where your environment matches your attestations and where it doesn’t, with each gap prioritized by claim-denial risk. You’ll know what to fix, what to document, and what to correct with your broker before renewal.
The findings are written for two audiences at once. Leadership gets plain language on what each gap means for coverage. Your MSP or internal IT gets remediation direction specific enough to execute without interpretation. And once the work is done, I verify it, so the fix is confirmed rather than assumed.
NO CONFLICTS
Independent Verification Is the Whole Point.
Your MSP can’t credibly audit its own work. Your carrier has a financial interest in finding gaps after a claim, not before. And every vendor offering a free assessment is pricing the remediation before they’ve finished the sentence.
I don’t sell hardware, software, or insurance policies, and I don’t take vendor commissions. The only thing this review produces is an honest answer to one question: would your coverage hold up if you needed it tomorrow?
That answer goes to the person who signs the application, because they’re the one carrying the risk.
HOW IT WORKS
From Application to Verified in 3 Steps.
Step 1: Gather. We pull your current policy, your application or renewal questionnaire, and prior loss runs if any. The application is the requirements spec, so everything gets measured against its exact wording.
Step 2: Verify. I assess each attested control against evidence, not assurances. MFA by enforcement report, EDR by coverage report, backups by restore test, training by completion records.
Step 3: Deliver. You receive the findings report and I walk leadership through it, gap by gap, with a prioritized path to fix or disclose each one before the application gets signed.
Most reviews complete within 2 to 3 weeks, depending on how quickly your IT provider produces evidence.
QUESTIONS
Common Questions.
Can cyber insurance deny a claim for missing MFA?
Incomplete MFA deployment can create a serious coverage issue when an application represented that MFA was implemented more broadly than it actually was. However, some carriers may allow you to disclose that MFA is not yet fully implemented and provide a planned completion date. Check with your insurance broker or carrier before answering, because application language and underwriting requirements vary.
What does a cyber insurance readiness assessment cost?
The Readiness Review starts at $2,500. The Readiness Engagement is scoped to your environment, since incident response planning and documentation depth vary by organization. Either way, you’ll have a fixed number before anything begins.
We have an MSP handling security. Don't they cover this?
Your MSP deploys and manages controls, but the attestation on the insurance application is yours, not theirs. This review verifies their work against your policy’s requirements, which is a different job than doing the work itself.
What if the review finds gaps?
That’s the point of doing it before a claim instead of during one. Gaps found now get fixed or disclosed to your broker. Gaps found by a forensic team after a breach get your claim denied.
How long does it take?
Most reviews complete within 2 to 3 weeks, depending on evidence turnaround from your IT provider.
We just had an incident. Is it too late?
If an incident has already occurred, follow your policy’s reporting instructions and contact your carrier or breach counsel immediately. Once the response is properly coordinated, I can support control validation, remediation planning and renewal preparation in collaboration with the authorized response team.
BEFORE YOU SIGN
Know What You're Attesting To.
Every renewal signed on unverified answers creates a unavoidable coverage risk. A 30-minute conversation is enough to determine whether an independent review would help you before you sign.