One chestnut from my history in lottery game development:
While our security staff was incredibly tight and did a generally good job, oftentimes levels of paranoia were off the charts.
Once they went around hot gluing shut all of the “unnecessary” USB ports in our PCs under the premise of mitigating data theft via thumb drive, while ignoring that we were all Internet-connected and VPNs are a thing, also that every machine had a RW optical drive.
It was for government owned computers, they didn’t want any pirated or virus-infected stuff, and at that point there was no way to lock down such a mish-mash of systems.
The software company (who also do things like run prisons these days) had given permission for us to run the software and given a set of fake data so we could go through the motions when talking people through things, but apparently that wasn’t enough to get it on the list.