Ontario Cyber Insurance in 2025: What Brokers Don't Always Spell Out

Let's be honest: nobody starts a business because they're excited to fill out a 14-page cyber questionnaire.

But if you've spoken with your broker lately, you've probably noticed two things:

• The forms keep getting longer
• The "minimum security requirements" keep getting tougher

Industry groups and insurers have been warning since at least 2022–2024 that cyber insurance is tightening in Canada. A 2023 self-assessment tool from the Insurance Bureau of Canada was basically a giant hint: "Get your house in order or you won't qualify."

Cyber Insurance 101 (The Straight Version)

For Ontario businesses, cyber insurance usually sits beside your commercial package. It's not legally required, but more contracts, landlords, and partners are quietly baking it into their expectations.

Typical coverage buckets:

• Incident response (forensics, legal, PR)
• Data restoration and recovery
• Business interruption (lost income while you're down)
• Third-party liability (customers, regulators)
• Sometimes extortion / ransom costs

Here's the catch: payouts are conditional. If you ticked "Yes, we use MFA everywhere" and you don't, you may be arguing with your insurer on the worst day of your career.

What Changed Between 2020 and 2025?

Carriers have been burned. Big Canadian breaches at retailers and critical services drove home that most organizations were underprotected.

By late 2024, several Canadian brokers were openly saying:

• Firewalls and antivirus alone don't cut it
• Insurers expect MFA, backups, and monitoring
• Questionnaires are basically risk audits

So in 2025, if you're a business along the QEW applying for or renewing cyber coverage, expect questions in five areas:

Identity & Access

• MFA on email, VPN, admin accounts
• Unique accounts (no shared "admin" logins)
• Password policy or manager in place

Backups & Recovery

• Offsite backups (cloud or secondary site)
• 3-2-1 style approach recommended by federal guidance
• Proof you've actually tested restorations

Endpoint & Network Protection

• Modern EDR/XDR or at least centrally managed AV
• Supported OS versions (no ancient Windows boxes)
• Logged and monitored firewalls

Policies & Training

• Written incident response plan
• Regular phishing or awareness training, which federal and legal guidance has been pushing for years
• Vendor management basics (who else touches your data?)

Prior Incidents

• Any ransomware, even "small," will trigger more questions
• What you changed since the last event

Where Hamilton's Situation Fits In

When Hamilton's ransomware costs started hitting local headlines, the price tag wasn't the part that worried me most. It was that a major organization could end up eating eight figures in costs if its controls didn't match what the insurer expected.

For smaller businesses, that same logic applies on a smaller scale. If your policy is worth $250K but your controls don't match what you declared, you may find yourself in a long argument while your business bleeds cash.

How to Get "Underwriter-Ready" Without Going Broke

If I were sitting across from you at a Tim's in Stoney Creek, here's the simple game plan I'd sketch on a napkin.

Step 1 – Ask your broker for last year's questionnaire

Don't wait for renewal. Get the form now and treat it like a to-do list:

• Highlight anything you can't answer confidently
• Circle anything that's technically true but fragile ("We have MFA… except for those three executives")

Step 2 – Fix the cheap stuff first

Low-cost, high-impact moves:

• Turn on MFA for email and remote access
• Standardize backups and test one restore
• Document a simple, clear incident response flow

Step 3 – Align your story with reality

Before you sign the next application:

• Make sure whoever fills it out talks to IT / your MSP
• Avoid "aspirational answers" – insurers have become very good at verifying after a breach
• If there's a gap, document your remediation plan rather than pretending it doesn't exist

Step 4 – Use security to negotiate, not just comply

Brokers and underwriters respond well when you show:

• Proof of MFA deployment
• Backup reports
• Training records
• A short security roadmap

You might not get a discount for everything, but you're a better risk than the company that just ticked boxes.

Bottom Line for 2025

If you're running a business in Hamilton, Burlington, Oakville, or anywhere in between, treat cyber insurance like this:

• Not a replacement for security
• Not guaranteed money
• Definitely part of your risk strategy

Do the basics right, document them, and your odds of both qualifying for coverage and getting paid when it counts go way up.