I have a few of these.

I asked to be excepted from a contract condition giving IBM first pick on any IP I develop in my own time.

Keep in mind, I was working in one of their technical support call centres. I had no access to IBM proprietary information, I had no role in developing it, I was a complete non risk on this front. I had more access to customer systems, no access to RED or BLUE networks, just an IBM lotus notes account I could use to slowly download information from HR.

Everyone I could physically speak to looked at my request and went, hey that's a really reasonable request.

It took 6 weeks for the first no to come back, my direct manager, whose stats I was apparently holding in place, apparently tried to intercede, adding 2 further weeks for a review. The answer was still no. This had apparently gone up through one line of reporting across to the US, branched out into legal and came back down that path. It was crazy.

So I left, so I could work on a small software project with a friend without risking IBM having an interest in it.

Another one. The HR forms were all written in the early 80s and digitised sometime in the 00s. Our team, not being customer facing, was super diverse. I know there was an attempt to try and get the HR forms updated to recognise other gender/pronoun combinations. This took like 12 weeks to be reviewed, and I think the eventual no was based entirely on the fact that no one wanted to try and figure out whose job it was to update the forms. Our team was full of LGBT people, and retention of them appeared to be critical. Hard no.

Also, our sexual harrassment training came on tape (in the year of our lord two thousand and ten) and implied that it was the updated version, previously it might have been vinyl or something.