In the good old days of floppy disks we had a clerk who had been put in charge of tracking contracts and licenses. She did not understand either and was not interested in learning anything about them. Even back then, a software license was printed on the envelope containing the disks. Despite being repeatedly asked to refrain, she would receive the software -- her real job was sorting the office mail -- open the box, pull out the envelope with the software and forward the empty box to the addressee.
If anyone complained to her, she would tell her manager, who knew even less about everything than she did, that she had been yelled at and berated. So there we would be, without our software and with a ding in our personnel files. Come to think of it, her real job may have been the office back-stabber. I hate the good old days.
Have you ever tried to deal with GPL code on your organization? Is an amorphous legal virus written in legalese that mutates with each new version and infects everything that it touches. The latest mutation is so harmful (business wise), that even Linux decided to not use it on its kernel and instead kept version 2 of the license.
This one hits close to home. I was working for a Fortune 10 company 20 years ago and we were evaluating a piece of software that we decided to purchase. Well the license agreement had to go to legal and our lawyer and the software vendors lawyer got into a pissing contest. The software sales department kept giving us temporary keys to use the software while the lawyers continued to argue. That went on for over a year before we finally got a signed agreement. And, after all that, we only used the software about one more year before we ditched that computing platform and went with Unix.
The only time I encountered such a thing is when I was working for an advertising agency. They made me send the EULA back-and-forth to the software vendor like a dozen times. It took a freaking month. When talking to the software vendor (and they were a huge international company), they said that they'd never had someone challenge their EULA before. The sales guy was sorta shocked.