Assuming this telling is pretty accurate, I'm wondering what the thinking was on both ends.

On the freeloader end: Did they think they were within the rules? How far up was the approval to keep doing it this way? Did someone try to pay, but get blocked? Did someone tell their boss they did this all in-house, and now doesn't want to admit they outsourced and exposed the company? Did it go to the top, and a lawyer told them to put the company name and a real person each time, and that they were covered on good faith if they only did that?

On the provider end: Seeing this locked-in enterprise user for 10 years, how was a salesperson not all over that that slam-dunk sale? How did they let this go on for 10 years without tweaking their policy to stop the freeloader and any others who might emulate them? What did the business people say about this over the years when it came up? Was business so good it wasn't worth the time to convert the freeloader to a paying customer?