I generate the licenses..
I'm on the other side of these conversations. My company sells permanent licenses for software but issues activation keys with expiry dates. The keys are somehow linked to the maintenance contract. It makes no sense and the bosses keep contradicting themselves about what the rules are.
So one day in a meeting the conversation came around to how to force users to upgrade. A boss said that we could do it via the key expiry date. He asked me what we would do with a request for a key to a Jurassic version. He wasn't impressed when I said that I would do whatever was necessary to get that client a key.
Software is weird.