What’s your Favorite Outlandish IT task?

Using a throwaway for this.... It was a campaign year, and my Boss very much does not jive with the local majority, including most of his own employees. Said boss decided he was going to plaster some of company properties with political signs of various sizes. That didn't quite go well with the local community who took it upon themselves to remove them. Boss would then replace them. Repeatedly. This went on for months... In case you didn't know, removing or defacing someone else's political campaign signs is an act of preventing someone else's freedom of speech. So boss got tired of it and went to the police... The company is easily the largest tax contributor to the city, so the police has always been helpful... so they asked for evidence. Which started an entire project.... At first we started with a crappy camera. Turned out most of these people were doing it at night and the camera wasn't quite good enough to get license plates at night... So I went and bought the nicest network camera with an enormous optical zoom to get real nice and personal images of the people. I spent several weeks basically going through footage every day since the signs would disappear and reappear multiple times a day, collecting evidence for the police. I don't think the police was actually interested in doing anything beyond appeasing my boss and didn't expect us to go this far. But it was far from over. Then came an interesting video of one of our own employees removing the signs.... I had to take that up with several layers other than the boss to figure out what to do about that. Way above my paygrade. I don't think anything came of it, thankfully. Finally, after not much action from the police since they aren't going to go after several people every day, and they aren't going to sit at the corner defending political signs for a political party they didn't agree with... Which started a bigger project of signs that are next to impossible to remove. They were built by our shop and were forklifted out. Then I got to watch people try to knock these down or punch them or beat them up for weeks. Unbelievable amounts of office entertainment, and I was actually doing what the boss wanted. I could have made an entire collection of hilarious ones with multiple people hanging off a sign to lower it down, only to get picked up by a forklift operator not 10 minutes later. People punching them and making themselves bleed, running away in shame. A few weeks later, someone got some spray paint... So the signs finally needed to be replaced again, and were outfitted with a spray paint resistant coating.... Which basically made the paint bead and not really stick. This continued until the election was all done for, at which point the signs got approved to be removed by us...