I had a coworker that NEVER restarted his computer or installed updates of any kind. Any time he showed me some code I got distracted by the "new updates are available" popup that was always there in his IDE.

I can't even imagine the backlog of critical security updates that were waiting to be installed when we left after 3 years.

My work's website being unsupported with Django security patches. I bring this up with management and say we should upgrade ASAP. Apparently that wasn't possible because the sysadmins refused to upgrade their old version of RedHat so we can't use anything that doesn't support Python 2.6.... To this day it still runs on Django 1.6.

Dealing with outdated tech whilst still being expected to perform miracles with it.