What Was Your Biggest Dumpster Fire in Your Technology Career?

I was just right out of school, didn't have a lot of experience and I was working on something pretty critical for the new for a large scale project at the time. One is probably more proud of is this kind of the OR mapping tool we built for JTE. That was before Hibernate. Later once we moved to Donnet, I was trying to port that code to a Donnet platform but didn't get too far into it. He should thank Eric Dohlenberg; he did most of the work.