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It wasn't "worst" in terms of how much time it wasted, but the worst in terms of how tricky it was to figure out. I submitted a change list that worked on my machine as well as 90% of the build farm and most other dev and QA machines, but threw a baffling linker error on the remaining 10%. It turned out that the change worked fine on any machine that used to have a particular old version of Visual Studio installed on it, even though we no longer used that version and had phased it out for a newer one. The code I had written depended on a library that was no longer in current VS installs but got left behind when uninstalling the old one. So only very new computers were hitting that, mostly belonging to newer hires who were least equipped to figure out what was going on.
That reminds me of when some of my former colleagues and I were on a training about programming industrial camera system that judges the quality of produced parts. I'm not really a programmer, just a guy who can troubleshoot and google stuff and occasionally hack together a simple code with heavy help from Google too.
The guy was a German (we are Czech and we communicated in English) programmer who coded the whole thing in Omron software but he also wrote his own plugin for it. All was well when he was showing us on the big screen, but when he sent us the program file so we could experiment on it (changing parameters, adding steps to the flow...) the app would crash. I finally delved into the app logs and with the help of Google I found it was because he compiled his plugin with debug flags and it worked for him because he had the VS debug DLLs installed but we didn't.
I feel a repressed memory or two stirring 😐