There are specialty insurance companies which cover specific risks and know how to evaluate them. The classic is The Hartford Steam Boiler Insurance Company.[1] They were the first insurance company willing to insure steam boilers. About half their employees are boiler inspectors. When they started, in 1866, nobody else would touch that business.
They inspect before they insure. Typically, they send inspectors and provide the boiler owner with a to-do list. Then they come back to see if everything was fixed. Only then does HSB write a policy. Their policies give them the right to come in at any time and inspect. Which, randomly, they do.
Boring old Hartford Steam Boiler is expanding into computer systems insurance.[2] But they are not as hard-ass about inspections as they are with boilers, unfortunately. They know how to keep boilers from blowing up. Computer security isn't there yet.
Can you share the name of the company?
When you have an attack that moves from your servers to your desktop computers, you have a network issue, which would be covered in an audit to verify you properly segment your network instead of having it in one large broadcast domain.
The open source model is benefiting too many businesses to just up and throw it out.