Cyber Insurance Readiness Checker

Cyber insurance applications now require granular evidence, not just unchecked boxes. When your security controls are scattered across disparate consoles and documents, proving readiness to an underwriter becomes a bottleneck. This skill translates insurer questionnaires into a structured evidence register, identifying where your MFA, backups, and endpoint protection actually stand against carrier requirements.

What it does

• Requirement Mapping: Extracts exact insurer questions and assigns unique identifiers to track compliance status.
• Evidence Validation: Audits screenshots, logs, and reports to distinguish between a "policy" and a "proven control."
• Gap Analysis: Identifies weak MFA coverage, missing restore tests, or stale evidence that could trigger a decline or premium hike.
• Remediation Planning: Generates prioritized task lists with acceptance criteria to close security gaps before submission.
• Drafting Support: Produces truthful, evidence-backed draft answers and flags specific items for broker clarification.

How it works

1. Define the Boundary: Supply the insurer form, policy schedule, and internal control records.
2. Extract and Map: The skill parses the questions and maps them to your existing evidence and custodians.
3. Assess Readiness: It classifies each control as Verified, Partial, Asserted, or Contradicted based on the data.
4. Export the Pack: You receive a full readiness register, remediation plan, and a broker follow-up list.

Frameworks & tools

Works with standard cyber insurance questionnaires (e.g., Travelers, Chubb, Beazley) and maps to controls found in EDR consoles, backup reports, identity providers, and incident response plans.

Why this beats prompting it yourself

Generic prompts often overlook the specific "gotcha" wording in insurance forms, like the difference between "MFA available" and "MFA enforced for all remote access." This skill enforces a conservative evidence-first logic, preventing accidental misrepresentations that could void your coverage.

Use cases

• Renewal Preparation: Audit current security posture 90 days before policy expiration to fix gaps.
• Application Hardening: Map evidence for a new carrier to ensure high confidence in the submission.
• Internal Compliance Audit: Test if IT assertions about backups or patching match the available documentation.
• Broker Handoff: Create a professional summary of open items and clarifications for your insurance broker.

Known limitations

Does not provide legal advice, bind coverage, or guarantee specific premium rates. Requires manual upload of evidence or control descriptions to function.