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.
They forbid us to add our ssh keys in some server machines, and force us to log in these servers with the non-personal admin account, with a password that is super easy to guess and haven’t been changed in 5 years.
VPN to another country and pretend to crack it. Repeat this until IT changes their mind.
Chaotic good.