A few years ago I ordered a custom license plate 'NULL'. What should have been a 2-3 week process lasted 8 months, with the order being canceled multiple times, and at one point a blank plate being shipped to the county clerk's office.

More recently I've gotten out of a parking ticket in a certain municipality when a frustrated meter maid told me they saw my plates were valid, but the handheld device used to issue tickets would crash any time they tried to issue the ticket.