Well, mine is a bit different.
So, my first time experimenting with macros, I recorded a lengthy session of an adventurer picking up a big stockpile of rocks, and throwing them back down. So my guy was sitting in some random woods, in sneak-mode, and I played my macro. It went ok, albeit much slower then just doing it manually, then I see a single approaching from the side. "No problem, I'll just cancel the macro and go smash this wolf".
Nope. The macro keeps playing, no matter what I do. The wolf attacks and displaces me to a grassy patch. Since it has "a" in the macro, over and over, I kept getting the announcement page coming up, blinking, while squeezing in commands to kill the damn wolf or something, which, in the process I managed to set fire to all the shrubs around with my arrow-key mashing to chase and kill this wolf while this damn macro is spamming other key commands.
So, I eventually get caught in the fires the macro was setting and I get "you are melting x59" before I ever kill the wolf and I die. That doesn't stop the macro, which is still hitting "t,t,enter" and on exiting advent mode, it selects my favorite fort save, which I'm suddenly looking at. Struggling to stop the madness, I manage to abandon the fortress.
Turns out I abandoned fortress on the only good save of a long-going project that set me back two weeks or so in IRL gameplay.
I manged to exit DF while the macro kept spamming "t,t,enter".
Not sure if that counted as "Fun" or not, but it certainly punished the crap out of me for inexperience, which is fun, I think.