There's a well-known site for stupidity wonders in software development, named DailyWTF. It's actually pretty nice, though sometimes I disagree with the editors. In either case, I have a whole bunch of programming WTF stories from my own environment(s). The following is a 2-year-old WTF from [some large financial organization, name withheld to protect the guilty].
We all heard about production software systems running in "debug" configuration, just because "they work better than their release counterparts". The later would crash, presumably because of higher chances to accidentally overwrite useful data in case of more dense static memory allocations.
This time it was something much more severe. ZM reports that he found a group working on a near-production version of a system, written on Visual Basic which they ran on a server with installed VB6 by means of "F5". They couldn't do it any other way, because their application ....would not compile.