School PC "hacking" and bypassing locking was a great past-time.
One of the schools I went to had a computer lab in the Library, ran on Windows NT 4. I found so many work-arounds to their security controls that they ended up making me an admin and told me to fix them all. That was my intro into group policies and domain management.
Another student made a credential-phishing program - it was a full-screen VB6 app that looked like the normal NT4 login. They'd log in, launch the credential-phishing app, and then walk away. It wrote the stolen creds to their 'home' drive and then logged out after showing some fake "There was a problem with your password, try again" message.
Many years later, but still on NT4/Windows 2000, at technical school we found that the campus-wide internet was run through a single Windows-based proxy, with rules on the router to prevent traffic to the internet except from that proxy.
They also did various content-filtering things, allowing only certain white-listed sites.
At that time Windows's networking was iffy - and if it detected that another computer was using the same IP, it'd disconnect itself from the network.
Our class had a computer lab with removable 3.5" drives and we were learning about setting up networks. Well, install a Linux distro, install squid with rules to allow all traffic. Then once it was working, change your machine's IP to that of the proxy. Now the entire campus's internet traffic was going via your lab machine, and you had free access to the internet. We just kept a 'proxy' disk around and put it in anytime we needed something that wasn't whitelisted. I don't know if the network admins either didn't care, or didn't know because it wasn't fixed for a few years.