Cybercrime isn’t just a nuisance anymore. It’s an industry. And business is booming. 

Two of the largest ransomware payouts last year were over $70 million. Let that sink in. That’s not just hitting the jackpot—it’s bigger than winning the lottery. Hackers see those numbers climbing, and just like a gas station full of people buying Powerball tickets, they’re lining up to cash in. 

But there’s another jackpot no one’s talking about—class action breach settlements. 

Google alone paid out over $300 million last year, and in the last 90 days, the number of settlements has doubled. The cost of getting hacked isn’t just downtime and lost data anymore—it’s legal fees, regulatory fines, and massive payouts to customers who suddenly see you as a walking ATM. 

Here’s the Ugly Truth: Cyber Insurance Won’t Save You Unless You Prove You Deserve It 

Yes, you need cyber insurance. Just like you insure your car, you should be insuring your data—because it’s worth a whole lot more. 

But here’s the kicker: Your insurance company expects you to act like a responsible business owner. They assume you’re using the cybersecurity equivalent of seatbelts—MFA, endpoint security, regular audits. 

More importantly, they expect you to prove it. 

Think about car insurance: If you crash your car but don’t have a valid license, weren’t wearing a seatbelt, or were texting while driving, your insurance company isn’t cutting you a check. Cyber insurance works the same way. If you can’t show documented evidence that you followed best practices, they’re walking away. 

How Do You Prove You’re Worth Protecting? 

You collect evidence—before the breach, before the lawsuit, before the insurance company starts looking for an excuse to deny your claim. 

  • Employee Training Records: Can you prove your team was trained on security best practices? Is that training linked to specific policies? 
  • Third-Party Audit Reports: If your insurer requires annual penetration testing, can you show them the test results, your review notes, and proof that you addressed vulnerabilities? 
  • Incident Response Documentation: When something bad happens, do you have a playbook, an incident log, and a response record that shows you handled it correctly? 
  • Policy Enforcement Evidence: It’s not enough to say you have MFA. You need logs showing it was enabled, used, and tested. 

When you walk into a breach response with reams of evidence showing you were proactive, your insurer fights with you. If you walk in with a pile of excuses, you’re fighting alone. 

Bottom Line: Protect Yourself Now or Get Burned Later 

Cyber events are not a matter of if—they’re a matter of when. You don’t get to opt out. But you do get to decide whether you’re the business that survives, or the one that gets buried in lawsuits and insurance denials.

Start gathering your evidence today. If you don’t have a cyber liability management program, implement one now—because by the time you need it, it’ll be too late.