Free cyber insurance readiness self-assessment · No signup required
Cyber insurance readiness assessment tool
Answer 10 plain-language questions and get a Wolferdawg readiness score, category breakdown, and prioritized checklist before you apply or renew. No login or sales call required.
Free cyber insurance readiness self-assessment
Use this quick check to review 10 security practices that can appear in cyber insurance applications. Answer based on what your business can verify today. Choose Partly when coverage is incomplete and No or not sure when evidence is missing.
- 10 questions
- About 4 minutes
- No signup
- Answers scored in your browser
This is not an insurance application. Requirements vary by carrier, policy, business, and renewal. Confirm every answer on the actual application with your licensed insurance broker and the person responsible for your technology.
Your score by category
Your prioritized readiness checklist
Where to go next
Email your score, grade, readiness band, verdict, and identified gaps. The submitted contact information and results are also copied to Wolferdawg IT Consulting. By clicking Email my results, you agree that Wolferdawg IT Consulting may retain your contact information and assessment results and contact you directly about your results and related services. You will not be added to a newsletter or bulk marketing list.
Need help verifying the technical answers?
Wolferdawg IT Consulting can document coverage for multifactor authentication, endpoint protection, backups, email authentication, patching, and other technical safeguards. Your insurer and licensed broker make the coverage decision.
Or call (580) 956-8424 or email hello@wolferdawg.io.
This is a self-reported educational readiness check based on 10 selected security practices. It is not an insurance application, quote, policy review, eligibility decision, premium estimate, audit, or legal or insurance advice. Only the insurer can make an underwriting decision. Review the actual application with a licensed insurance broker.
How the cyber insurance readiness score works
The percentage, letter grade, and readiness band are Wolferdawg diagnostics. They are not carrier scoring rules or predictions of coverage. Yes, fully earns all available points. Partly earns half. No or not sure earns zero and creates a finding.
| Category | Available points | Share of score |
|---|---|---|
| Priority application controls | 16 of 28 | About 57% |
| Operational safeguards | 8 of 28 | About 29% |
| Data and financial safeguards | 4 of 28 | About 14% |
| Percentage | Base grade | Priority-control rule |
|---|---|---|
| 90 to 100% | A | One priority control answered no or not sure caps the final grade at C. Two or more cap it at F. |
| 80 to 89% | B | |
| 70 to 79% | C | |
| 60 to 69% | D | |
| Below 60% | F |
Why the grade cap? A high total can otherwise hide a missing safeguard this tool gives extra weight. This rule belongs only to Wolferdawg's readiness model. It does not represent a carrier's underwriting formula.
What cyber insurance applications may ask about
Applications vary. Depending on the carrier and policy, questions may cover your business, revenue, industry, sensitive data, prior incidents and claims, vendors, requested coverage, and technical or operational safeguards.
For example, Travelers publishes separate long-form, short-form, renewal, multifactor-authentication, healthcare, payment-card, and other cyber insurance forms. That is why no general self-assessment can determine whether a specific business qualifies. Review the current Travelers CyberRisk applications and forms as one carrier example. Coalition likewise states that eligibility is determined during the quote or renewal process using multiple underwriting factors. See Coalition's underwriting disclosure.
Security measures still matter because they reduce business risk, even when an individual application does not ask about every item. The CISA small and medium-sized business resources provide additional federal cybersecurity guidance.
Privacy, data use, and limitations
Your yes, partly, and no or not sure answers are scored in your browser. When results appear, the usage record includes the request time, IP address and approximate location, grade, score, readiness band, and total gap count. It does not include individual answers or identified gaps.
If you request an emailed report, the name, email address, business name, score, grade, readiness band, verdict, and identified gaps are submitted to the mail service and copied to Wolferdawg IT Consulting. By requesting the report, you agree that Wolferdawg IT Consulting may retain your contact information and assessment results and contact you directly about your results and related services. You will not be added to a newsletter or bulk marketing list.
Do not enter sensitive or regulated information. The assessment requires only multiple-choice answers. Do not place passwords, account numbers, customer records, health information, claim details, or other confidential information into the optional email fields.
Founder, Wolferdawg IT Consulting. 27+ years of IT and cybersecurity experience. Content reviewed August 25, 2026.
Prepare accurate answers before you apply or renew
- Get the current application from your licensed broker instead of relying on an older form.
- Send technical questions to the person or provider who manages the affected systems.
- Verify scope. A control that covers some users, devices, or systems may require a partial or qualified answer.
- Collect supporting records that the carrier requests, such as authentication coverage, endpoint coverage, backup and restore results, patching reports, policies, or incident response documentation.
- Have the authorized representative and broker review the complete application before submission.
Need help documenting the technical controls? Schedule a 30-minute call or contact Wolferdawg IT Consulting at (580) 956-8424.
Cyber insurance preparation resources
Related free cybersecurity tools
Common questions about cyber insurance readiness
Plain answers about underwriting, application evidence, scoring, privacy, and what this tool can and cannot determine.
What does cyber insurance underwriting examine?
Underwriting varies by carrier and policy. Applications may ask about business size, industry, data, prior incidents and claims, requested coverage, vendors, and security practices such as multifactor authentication, backup and recovery, access control, encryption, patching, incident response, and training. The insurer and licensed broker determine what applies to a particular application.
Does every cyber insurer require the same security controls?
No. Requirements and application questions vary by carrier, policy, industry, business size, location, data handled, claims history, and other underwriting factors. They can also change at renewal. Use the actual application and work with a licensed insurance broker instead of treating a general checklist as universal.
Does a high score mean my business will qualify for coverage?
No. This score is a Wolferdawg diagnostic based on 10 selected security practices. It is not an insurance quote, application, eligibility determination, coverage promise, or premium estimate. Only the insurer can make an underwriting decision after reviewing the complete application and other relevant information.
How is this self-assessment different from an insurance application, risk assessment, or audit?
This self-assessment scores 10 answers and identifies areas to verify. An insurance application asks the questions selected by that carrier and becomes part of the underwriting record. A risk assessment evaluates threats, vulnerabilities, likelihood, impact, and safeguards. An audit or evidence review verifies whether stated controls are documented and operating.
How is the cyber insurance readiness score calculated?
The 10 questions carry two or four points under Wolferdawg's model. Yes, fully earns all available points. Partly earns half. No or not sure earns zero and creates a finding. The maximum is 28 points. Priority application controls contribute 16 points, operational safeguards contribute 8, and data and financial safeguards contribute 4. One missing priority control caps the grade at C, and two or more cap it at F.
What information does the assessment record?
Answers are scored in your browser. When results appear, the usage record includes the request time, IP address and approximate location, grade, score, readiness band, and total gap count. It does not include individual answers or identified gaps. If you request an emailed report, the name, email address, business name, score, grade, readiness band, verdict, and identified gaps are submitted to the mail service and copied to Wolferdawg IT Consulting. By requesting the emailed report, you agree that Wolferdawg IT Consulting may retain your contact information and assessment results and contact you directly about your results and related services. You will not be added to a newsletter or bulk marketing list.
What evidence should I prepare for a cyber insurance application?
The exact evidence depends on the carrier. Useful records may include multifactor-authentication coverage, endpoint-protection coverage, backup configuration and restore-test results, patching reports, security policies, training records, an incident response plan, vendor controls, and documentation for prior incidents. Confirm the requested evidence with your broker and application.
Why must cyber insurance application answers be accurate?
An authorized representative may be asked to confirm that application answers are true and complete after reasonable inquiry. Do not guess. Verify technical answers with the person or provider responsible for the systems, explain partial coverage accurately, and notify the broker or insurer when the application requires disclosure of material changes.
Turn uncertain answers into documented evidence
Wolferdawg IT Consulting can verify your technical safeguards and help you prepare accurate information for your broker and insurer.