The Ten-Day Answer Services vCISO Advisory Leadership Baseline Cyber Insurance Readiness HIPAA Risk Assessment Risk Assessment MSP Security Oversight Industries Healthcare Financial Services Manufacturing & Logistics Legal & Professional Construction Defense Suppliers Locations Tacoma & Pierce County Spokane & Eastern WA Coeur d'Alene & North Idaho Resources Free Insurance Readiness Checker Cyber Insurance Application Guide Security Questionnaire Guide What a vCISO Costs vCISO vs MSP WA My Health My Data Act FTC Safeguards Rule Blog For MSPs & MSSPs About Community Contact Get a Ten-Day Answer
Get a Ten-Day Answer Call
Home › Resources › Cyber Insurance Application Questions

How to answer cyber insurance application questions

A control-by-control guide to what carriers commonly ask about MFA, EDR, backups, and the rest: what each question really means, what a defensible yes looks like, what evidence to keep, and where honest companies get tripped up.

What is a cyber insurance application really asking?

A cyber insurance application is a statement of fact about your security controls, signed by someone at your company. The carrier uses it to decide whether to offer coverage and on what terms. Each question asks whether a specific control exists, how far it reaches, and whether you could show it if asked.

That last part matters most. The person signing is usually an executive who did not configure the controls. The answers often come from an IT provider or MSP answering quickly, from memory, about a question worded differently than last year. Most bad answers are not lies. They are reasonable guesses that turn out to be broader than reality.

The rule for every question below is the same: answer what is true today, for the scope the question asks about, and keep the evidence. If you are unsure where you stand, the free cyber insurance readiness checker walks through these areas in a few minutes.

The control areas carriers commonly ask about

Wording differs by carrier and changes from year to year, so read your actual form closely. These are the areas that come up most often, and how to answer each one.

1. Multifactor authentication (MFA)

  • What it is really asking: Can a stolen password alone get someone into your email, your network from outside, or your admin accounts? Many forms ask about each separately.
  • A defensible yes: MFA is enforced, not just available, for every user on email, for all remote access (VPN, remote desktop, remote support tools), and for every privileged or admin account, including cloud admin consoles.
  • Evidence to keep: Screenshots of the enforcement policy, a list of any excluded accounts with the reason, and the date of your last review.
  • Common trap: Answering yes because Microsoft 365 email has MFA, while the VPN, the firewall admin login, a backup console, or a service account does not. Legacy email protocols that bypass MFA are another quiet gap.

2. Endpoint detection and response (EDR)

  • What it is really asking: Do you have software on your computers and servers that detects suspicious behavior, and is someone actually watching the alerts?
  • A defensible yes: A named EDR product is deployed on all workstations and servers, and alerts go to a person or provider who responds, including nights and weekends if the form asks.
  • Evidence to keep: A deployment report showing device coverage against your asset list, and a short note on who monitors alerts and how.
  • Common trap: Calling traditional antivirus EDR, or answering "100 percent coverage" when servers, laptops that rarely connect, or a few machines at a second site were never enrolled.

3. Backups: offline or immutable, and tested

  • What it is really asking: If ransomware encrypts everything an attacker can reach, do you still have a copy they cannot reach, and have you proven you can restore from it?
  • A defensible yes: Critical systems are backed up to a copy that is offline, immutable, or otherwise separated from your normal admin credentials, and you have performed a real restore test recently.
  • Evidence to keep: The backup schedule, a description of how the protected copy is separated, and a dated restore test record showing what was restored and how long it took.
  • Common trap: Saying backups are tested because jobs report success. A successful job is not a restore test. Another trap is cloud sync, which can faithfully copy encrypted files.

4. Patching and end-of-life systems

  • What it is really asking: How quickly do you apply critical updates, and are you running anything the vendor no longer supports?
  • A defensible yes: A documented patch window for critical updates that you actually meet, and either no unsupported systems or a list of them with how each is isolated.
  • Evidence to keep: Patch compliance reports from your MSP, and an inventory that flags operating system and firmware versions.
  • Common trap: Forgetting the old server running one line-of-business application, a machine on the shop floor, or network equipment nobody patches because it "just works."

5. Privileged access

  • What it is really asking: Who holds admin rights, are those rights separate from everyday accounts, and are they protected and reviewed?
  • A defensible yes: Admins use separate accounts for admin work, users do not have local admin rights, shared admin passwords are stored in a vault, and the list of admins is reviewed on a schedule.
  • Evidence to keep: A current list of privileged accounts with owners, and the date and result of the last access review.
  • Common trap: Former employees or a previous IT provider still in the domain admin group, or an owner whose daily email account is also a global admin.

6. Email security and phishing training

  • What it is really asking: Do you filter malicious email, protect your domain from spoofing, and train people to spot and report phishing?
  • A defensible yes: Email filtering is in place, SPF, DKIM, and DMARC are configured for your domain, and everyone completes training with periodic phishing simulations.
  • Evidence to keep: DNS records, training completion reports, and simulation results by date.
  • Common trap: A DMARC record set to monitor only, or "annual training" that last ran two years ago and never reached new hires.

7. Incident response plan

  • What it is really asking: If you were hit tomorrow, do you know who decides what, who you call first, and how you reach your carrier's breach hotline?
  • A defensible yes: A written plan with named roles, contact details that work when email is down, and the carrier notification steps. Ideally it has been exercised in a tabletop exercise.
  • Evidence to keep: The dated plan, its approval, and notes from the last exercise.
  • Common trap: Pointing to your MSP's internal runbook. That covers their technical steps, not your business decisions, legal notifications, or carrier contact. Our incident response plan service exists for exactly this gap.

8. Vendor and remote access

  • What it is really asking: Which outside parties can reach your systems, how, and is that access protected and limited?
  • A defensible yes: You know every vendor with remote access, each uses named accounts with MFA, and access is turned off when not needed.
  • Evidence to keep: A vendor access list with the tool each uses and the date it was last reviewed.
  • Common trap: An equipment vendor or software support company with an always-on remote tool and a shared login that nobody remembers approving.

9. Wire transfer and funds verification

  • What it is really asking: If someone emails a request to change bank details or send an urgent payment, does a human verify it through a separate channel before money moves?
  • A defensible yes: A written procedure requiring a call-back to a known phone number (not one in the email) for any new payee or bank change, with dual approval above a set amount.
  • Evidence to keep: The written procedure, staff acknowledgment, and a log or note showing it is followed.
  • Common trap: "We always call" as an unwritten habit of one bookkeeper. This matters a lot in construction and real estate, where large payments to new parties are routine.

Why do inaccurate answers matter at claim time?

The application usually becomes part of the basis for your policy. After a claim, a carrier may compare what you said against what investigators find. If an answer was wrong in a way that mattered to the decision to insure you, often called a material misrepresentation, the carrier may have grounds to dispute or limit coverage.

How that plays out depends on your policy wording, the facts, and the law that applies, so treat this as general background only. This is not legal advice; ask your broker or attorney about your specific policy.

The practical point is simple. The worst time to discover that MFA did not cover the VPN is during a ransomware investigation, when the forensic report shows the attacker came in through the VPN. An accurate "no, with a remediation date" is a conversation with your broker. An inaccurate "yes" can become a coverage dispute at the moment you most need the policy.

Pre-Renewal Timeline

When should you start preparing for renewal?

Start about 90 days before your renewal date. That leaves time to confirm controls, close small gaps, collect evidence, and answer follow-up questions without rushing the signature.

90 days

Get the form and check reality

Ask your broker for this year's application, since questions change. Walk through each control area with your IT provider and mark every answer you cannot back with evidence.

60 days

Fix what you can, date the rest

Close quick gaps like MFA exclusions, stale admin accounts, or an untested restore. For larger items, set an owner and a realistic completion date. Collect screenshots and reports.

30 days

Answer, review, and sign

Draft final answers, have the signer review the evidence behind each yes, and send the application to your broker with notes on any gaps and their dates.

What should you do if the honest answer is no?

Answer no, then show the carrier you have a handle on it. Describe any compensating control that reduces the risk, give a specific remediation date with an owner, and tell your broker early. A known gap with a plan is a conversation with your broker; a yes that does not hold up is a problem at claim time.

  • Compensating controls. If one legacy system cannot support MFA, explain what limits exposure, such as no internet access, a restricted jump host, or network isolation. Be specific and be accurate.
  • Remediation dates. "In progress" means little to an underwriter. "MFA on the VPN by March 15, owned by our MSP, project already scheduled" means a lot. Only give dates you can meet.
  • Talk to your broker first. Your broker knows how different carriers treat specific gaps and may know where a supplemental form or explanation field helps. Do not let them be surprised by a no on submission day.
  • Write it down. Keep a short gap register: the question, the honest answer, the compensating control, the owner, and the date. It keeps next year's application consistent with this one.

This is exactly what the Ten-Day Answer produces: the completed application, a gap register with an owner and date for every non-clean answer, and a one-page remediation plan your MSP can execute. For broader preparation, see cyber insurance readiness.

Get It Answered

Renewal coming up? Send us the application.

The Ten-Day Answer is $3,500, fixed fee, ten business days, one document. We work from interviews with you and your IT provider, never touch your systems, and sell no products or coverage. We help businesses across Washington and North Idaho, including Tacoma and Pierce County, Spokane, and Coeur d'Alene and North Idaho, and clients in healthcare, manufacturing, and financial services.

We do not guarantee approval, coverage terms, or premiums. Those decisions belong to the carrier.

Frequently Asked Questions

Cyber insurance application questions, answered.

Applications commonly ask about multifactor authentication, endpoint detection and response, backups and restore testing, patching and end-of-life systems, privileged access, email security and phishing training, an incident response plan, vendor and remote access, and how you verify wire transfers and payment changes. Wording varies by carrier, but these control areas show up again and again.

Only if the question is scoped to the part you have. If the question asks whether MFA is required for all remote access and one VPN account is exempt, the accurate answer is not a plain yes. Answer what is true, add a short explanation if the form allows it, and talk to your broker about how to present the gap.

Someone who understands the questions and can confirm each answer with your IT provider or MSP. The person who signs is usually an officer of the company, so they should see the evidence behind each yes before they sign. Your broker submits the application but generally cannot confirm your controls for you.

It depends on your policy language, the facts, and the law that applies. In general, a carrier may look closely at application answers after a claim, and a material misstatement can give it grounds to dispute coverage. This is not legal advice. If you find an error, tell your broker promptly and ask how to correct the record.

About 90 days before the renewal date. That leaves time to confirm your controls, fix small gaps, collect evidence, and get the application to your broker with room for follow-up questions. Starting at 30 days usually means answering from memory, which is where errors come from.

No one can promise that. Pricing and coverage decisions belong to the carrier and depend on many factors. Accurate answers backed by evidence help you avoid surprises at claim time and give your broker a clearer story to present, which is worth doing regardless of price.

No. CyberCascadia is advisory only. We do not sell products, earn vendor commissions, or touch your systems. We help you answer accurately and give your IT provider or MSP a clear list of what to fix.

Often, yes. The Ten-Day Answer is a $3,500 fixed-fee engagement that returns one completed application in ten business days, with a gap register and a remediation plan for your MSP. We confirm on the intake call whether the deadline and document are a fit.

Something security-related landed on your desk?

Send it to us. One questionnaire, insurance application, or contract exhibit, answered in ten business days for a fixed $3,500.