An 18 year old bug
I got a fun email earlier today - a support request for literally the second piece of software I ever wrote, back in 2001 when I was a kid with a couple months of programming under my belt.
It's a click tracker that I called Click Manager. Pretty simple stuff - a Perl CGI script that counts how many times a link was clicked, storing the data in a flat file database.
Eventually I even added a nifty UI to view the stats. Check it out, in all its early 2000s glory:
Anyway, point is, someone emailed me about a bug in Click Manager. That absolutely made my day, to learn that somebody was still using my old script.
I took a look at it. Turns out he was using version 2.2.5, from 2003. That is not the latest version though! The latest version is version 2.2.6, from 2005. (You can actually still download it from my website, but I like linking to those nice old layouts that archive.org has saved.)
After looking at a diff between version 2.2.5 and 2.2.6 (this was back before I used version control) it became clear that the only thing version 2.2.6 did was fix the exact bug he emailed me about!
Moral of the story: please update your software at least once per decade, or this might happen to you :)