Speaking in very general terms, let's just say that we've had to maintain an extremely locked down machine running a version of sshd from about a decade ago hosted in its own DMZ, all for one particular partner. It is monitored for everything we can think of, and I still find myself stressing about possible ways someone could escape from that machine - I'm mostly surprised we haven't been attacked through them yet.
Their problem is they bought proprietary software that's no longer supported, and look at it as a one-time purchase rather than a forward commitment. Our problem is the nontechnical relationship is important and we can't cut them off.
How the heck is this not criminal fraud? Why are people allowed to simply bill whatever they feel like it, and why is my mother getting 'balance billed' for random amounts? They're still doing all this dirty underhanded stuff and when they get called out on it, it's 'Oopsie! Our mistake' when they know most people they do this to will naively pay it
This has to be done in person, where they can't be, uh, accidentally disconnected, but I've found the rate-of-return on that time hard to beat. They discover all sorts of "mistakes" when you're taking up their billing specialists' time.
It is a bit like haggling over your car price after you already bought it; the main thing to get over is the social discomfort of being a pain in the ass, so they can't use that against you.