Here's how I think it went.
The Universal Financial Corporation won a back-off among all the major insurance carriers to provide property total loss stellar ship insurance to all pilots who are members of the Pilots Federation. The Pilots Federation, in exchange, pays an amount per member of the Pilots Federation, which they pay for by taking a cut of every piece of cartographics data and every bounty handed in by every Pilots Federation pilot. The contract is good for thirty years.
At first, everything went fine; the Universal Financial Corporation (UFC) made hefty profits, as most pilots, in the circumstance where there ship was destroyed, were inevitably killed themselves, and therefore unable to collect on the insurance. For the first few years, everything well for UFC; the underwriters were happy, everyone was happy.
What UFC didn't anticipate was rapid progress in Remlok and escape pod technology. By 3301, Pilots had a near certainty that they would survive even a total loss of ship, leading to a far greater number of claims tham UFC ever anticipated. UFC was forced to honor their contract, even as it dragged down the profits off the whole corporation.
Compounding the problems for UFC were the costs of compliance; insurance is regulated at the system level, driving up mind-numbing costs in the realm of billions of credits just to manage the compliance staff to process claims. Other services were offered to Pilots Federation Pilots, included generous loans at low interest rates, to try to balance the losses, but those have proven to not fully correct the problem.
The open question then is how long before UFC itself goes bankrupt, and what will happen after insurance rates have to be purchased on the open market, given Pilots Federation members proclivity for risky behavior?