The renewal questionnaire that lands on your desk this year reads less like an insurance form and more like an IT project plan — MFA everywhere, EDR on every machine, backups you’ve actually tested. Here’s how to make sure you get a vote before your underwriter decides your roadmap for you.
By Jonathan Eubanks · June 22, 2026 · 8 min read
⚡ The short version
I got a call last week from an owner who runs a handful of locations across Ohio. He wasn’t calling about phones or internet. He was calling because his cyber-insurance renewal questionnaire had just landed, and it read like somebody had photocopied an IT department’s wish list and stapled it to a bill. Multi-factor authentication on everything. EDR on every endpoint. Encrypted, immutable backups that he could prove he’d restored in the last 90 days. “I just wanted to keep my policy,” he said. “Now I’ve got a project list I didn’t ask for.”
Here’s what I told him, and it’s the thing I think every business owner needs to hear before their own renewal shows up: your underwriter is now writing your IT roadmap. The controls insurers demand in 2026 aren’t suggestions you can argue your way out of — they’re the price of having a working policy, and most of them live on your network, not in a piece of software you can buy on a Friday. The questionnaire isn’t a nuisance. It’s a deadline with a dollar figure attached.
I’ve been on the customer side of these decisions since 2003, and I’ll tell you the same thing I told him: this is actually a gift, if you treat it right. Someone just handed you a prioritized security plan and a hard date. The only question is whether you build it on your terms now, or scramble to check boxes the week before renewal and hope the cheapest fix holds up when a claim is on the line.
The questionnaires have gotten specific, and they’ve gotten strict. A few years ago an insurer might have asked whether you “had a firewall” and moved on. Now they want evidence. The three that show up on nearly every renewal I see are worth understanding before you answer them.
Multi-factor authentication, everywhere. Not just on the front door — on remote access, on email, on every administrator account. And increasingly, text-message codes don’t count anymore; insurers have caught on that SMS is the weak link attackers phish around, so they want app-based or hardware MFA. If you’ve got one old VPN or a legacy admin login that slips past MFA, that’s the gap the questionnaire is built to find.
EDR on every endpoint. Plain antivirus isn’t the answer to this question anymore. Insurers want endpoint detection and response — monitored, managed, actually watching for the behavior of an attack instead of just matching known virus signatures. The catch is the word “every.” The forgotten machine in the back office, the server nobody logs into, the laptop a contractor still has — those are exactly the endpoints that turn a yes into a no.
Backups you’ve actually tested. This is the one that trips people up the most. It’s no longer enough to say you have backups. The 2026 renewals want immutable backups — copies an attacker can’t reach and encrypt along with everything else — and they want proof you’ve restored from them recently. “We back up nightly” and “we have successfully restored in the last 90 days” are two completely different answers, and only one of them keeps your rate from jumping.
Most owners focus on the premium. That’s the wrong thing to worry about. Yes, missing these controls can push your renewal up 50 to 100 percent or more — that’s real money and it stings. But the premium is the survivable problem. The one that ends businesses is the denied claim.
Here’s how it happens. You attest on the questionnaire that MFA is enabled everywhere. A year later, an attacker gets in through the one account that didn’t have it — the legacy login you forgot about, the exception somebody made “just for now.” You file the claim. And the insurer points to your own attestation and declines to pay, because the control you said you had wasn’t actually in place where it mattered. You paid premiums for years for coverage that evaporated on a technicality you signed.
I’m not telling you that to scare you into a policy. I’m telling you because it changes how you should answer the questionnaire. Every box you check is a promise you’re making about your network — one you may have to prove on the worst day of your business’s life. So the goal isn’t to find the cheapest way to make the form say yes. The goal is to make the yes true, and keep it true.
Here’s what the insurance brokers don’t always spell out: almost none of these controls live in a single app you can install and forget. They live in how your network is built. MFA everywhere means you actually know every door into your systems — every site, every remote connection, every admin account — which means you need a clear map of your network before you can honestly say it’s covered. EDR on every endpoint means something is monitoring those endpoints across all your locations, which is a managed-service question, not a one-time purchase. Immutable, tested backups mean storage that’s segmented away from the systems it’s protecting, so ransomware can’t eat the backups along with the originals.
The questionnaire quietly assumes you’ve got a network designed for all of this — segmented, monitored, with secure connectivity between sites and a real inventory of what’s connected. For a single office, that’s manageable. For a business running six, ten, a dozen locations, it’s exactly the kind of thing that’s easy to half-do and hard to prove. And “half-done” is the same as “no” when the underwriter is reading your answers.
Quick win: Before you answer a single question on the renewal, do one honest inventory — every location, every way into your systems, every device that touches your network, and where your backups actually live. Most owners can’t produce that list, and that gap is the answer to half the questionnaire. You can’t attest to controls on a network you can’t see, and you certainly don’t want to find the blind spot the same week a claim depends on it.
If that inventory feels like more than you want to take on alone, that’s the first thing we do for a business heading into renewal — map what you have, line it up against what the questionnaire is asking, and show you where the real gaps are before you sign anything. Because the carriers and providers pay us, there’s no advisory fee for that look. We have no quota pushing you toward any one fix, which means we can tell you when you’re already fine. Talk to the team if you’d rather have a second set of eyes before the deadline picks your priorities for you.
If you’re in a regulated industry, the insurance questionnaire isn’t the only place these demands are showing up — and that’s actually good news, because it means one round of work satisfies more than one master. For financial and professional-services firms, the SEC’s amended Regulation S-P came into force for smaller firms on June 3, 2026: a formal incident-response program, client notification within 30 days of a breach, real oversight of your vendors, and multi-year recordkeeping. Read those requirements and you’ll notice they describe the same network — segmented, monitored, with secure connectivity — that your insurer is asking about.
Healthcare is on the same path. The direction of the 2026 HIPAA Security Rule updates points hard toward prescriptive controls — MFA, encryption of patient data both at rest and in transit, network segmentation, regular vulnerability scanning, and tested backups. I’ll be straight with you: a lot of the exact control lists floating around right now come from IT-vendor blogs rather than the final rule text, so treat the specifics as directional until they’re confirmed. But the direction itself isn’t in doubt, and it’s the same direction as everything else — especially when healthcare remains the number-one ransomware target in the country, where for a small practice an attack isn’t an IT headache, it’s an extinction event.
The point is that your insurer, your regulator, and frankly common sense are all converging on the same short list. You’re not chasing three different roadmaps. You’re building one network that’s actually defensible, and then pointing every questionnaire at it.
The renewal questionnaire feels like a burden because it arrives as a demand with a deadline. But strip away the framing and what you’ve actually been handed is a prioritized, expert-vetted list of exactly what your network should look like in 2026 — written by people who pay out when it’s wrong. That’s not a bad roadmap. The mistake is letting the underwriter’s timeline and the cheapest box-checking fix decide how you build it.
So get ahead of it. Do the honest inventory before you answer. Make the yes’s true, not just convenient, because you may have to prove them on the day it matters most. Treat the financial, healthcare, and insurance requirements as one network problem instead of three. And decide what your security should look like on your terms — this quarter, calmly — instead of the week before renewal with a number on the line.
If your renewal is coming up and you want a straight read on where you actually stand before you sign that attestation, that’s exactly the work we do, and it costs you nothing. Sometimes the answer is “you’re in good shape, sign it,” and we’ll tell you that too. Either way, you’ll answer the questionnaire knowing it’s true — which is the whole game.
— Jonathan
Jonathan founded Buckeye Telecom in 2003 after years in the Columbus telecom industry — first at 5-Star distributors learning the carrier side, then carrying his own quota in telecom sales. He still works directly with clients — backed by the Buckeye team.
Talk to the Buckeye team — the owner is involved in every engagement, and there’s no advisory fee.
Prefer to talk now? Call or text 614-224-2003.