My first "hack" was just a boot disk that simply copied fortress.exe to another directory (a little choice.exe with autoexec.bat magic).
The second hack came later. The computers were upgraded to Windows 98 and my autoexec.bat trick stopped working because of a BIOS password. Thankfully the machines came with Word which had nice shinny feature called Visual Basic for Applications. Most of the shell was hacked to hide menues still in Fortres 2.0 but good old VBA was still accessible. Using VB I could call Win32 apis and it was just a few calls to enumerate and kill the startup entries for fortress in the registry.
The best part of this was that it was all sanctioned activities sort of. The IT department was in a central building downtown (30 minutes away from our school) and who was always a pain to work with for the teachers. Their gradebook apps failed under fortress and even their teacher passwords failed to disable all the shell hacks. Shutting off fortress was the only compatible way to get things to run correctly for the teachers.
At first when the local IT department found out, they laughed, but then later got upset when the disk of my magic word document spread. It was making it's way across the district via email lists.
At some point in the school year I got accused of spreading 'a virus' to other students that allowed them to download 'warez' on school computers. Apparently fortress was the only thing preventing kids from using WinPopUp and windows NT messenger to send broadcast messages to all desktops across the network.
I tried to fight it and explain exactly how the thing worked and the silliness of shell hack in the first place. It didn't work. The Principal said I was hacking regardless and suspended me. After getting the suspension (and after they called my parents who knew before I did and were very upset already), I quickly called the computer programming teacher (who knew knew C++ and VB and had previously been an assistant for in my sophomore year). He called the principle and super and explained that I was not hacking and that I was 'improving productivity' and that the IT department's policies were hindering teachers. I got out of the suspension by the super the next day but no apology was given. Just a stern "stop hacking" the next week when I got back.
I was later voted most likely to succeed by my class. Apparently in a class size of 1200+, I was well known for my exploits.