Hacker’s Corner: Cyber Insurance – Your New Weakest Link?

If you want to understand how hackers think about cybersecurity insurance, you have to start with a simple truth: They don’t fear it. They exploit it.

Let me tell you about a real-world case — and what it taught the hacking community.

Back in 2020, the ransomware group Maze (you might remember them — slick, professional, and vicious) pulled off a series of attacks against companies across Europe and North America. Their tactic wasn’t just about encrypting files and demanding payment anymore.

They evolved.

Maze started stealing data first, then encrypting the systems, and then — here’s the critical part — researching the victim’s insurance policies.

You see, many companies were proudly advertising in their SEC filings or investor updates that they had “robust cybersecurity insurance.” Some even went so far as to post details about coverage limits. From a hacker’s perspective, that’s not just corporate news — that’s a price tag.

Maze and other groups realized: If you know a company is insured, you can demand a ransom just under their policy limit. That way, the insurer is more likely to pay quickly — and the victim feels less pain.

And it worked.

Several firms paid seven-figure ransoms, and in more than one case, insurance helped cover the cost — exactly as Maze had planned. (A French IT services company and a major U.S. law firm were among the rumored payouts linked to this playbook, though official sources stayed tight-lipped.)

What Hackers Learned

• Insurance disclosures are intelligence. Public or leaked information about cyber insurance coverage gives attackers a blueprint for how aggressive they can be — and how much they can demand.

• Timing matters. Hit them right after renewals, when coverage is fresh and limits are at their highest.

• Negotiation leverage shifts. If the victim has insurance, the psychological barrier to paying the ransom drops. “It’s covered,” they tell themselves.

How They Still See It

Even today, cyber gangs operating under names like LockBit, BlackCat, and Clop still probe during initial infiltration. If they land access to financial files, vendor agreements, or insurance certificates, they prioritize those documents. It’s not just about stealing emails anymore — it’s about understanding the payout landscape before making demands.

In fact, the U.S. Department of Treasury’s Financial Crimes Enforcement Network (FinCEN) even noted in a 2021 report that ransom amounts often align suspiciously well with insurance coverage levels.

Coincidence? Not likely.

If You’re Defending, Here’s What You Should Know

1. Treat cyber insurance documents like crown jewels. They need the same level of access controls as financials or sensitive client data. If a hacker finds them, your negotiation power just evaporated.

2. Limit public disclosure. Don’t brag about your cyber coverage unless you’re ready to paint a target on your back.

3. Expect smarter adversaries. Ransomware groups aren’t just deploying malware. They’re running recon, reading your policies, and planning their attacks with an insurer’s payout process in mind.

In short: Cyber insurance can save you from financial disaster after a breach.

But to hackers? It’s often just another tool — and another weakness, if you don’t treat it with the caution it deserves!