Here's half a dozen potential 'get out of jail free' plot devices. They could maybe be done once or twice with some entertainment value I'd think.
Young Guns style: the rest of the party busts your ass out of lockup with bolts and arrows blazing hehe. That's kinda the default, anytime a lone PC gets nabbed, since its pretty simple. Fight your way out!
Young Guns 2 style: similar to the above, but with an inside man hehe.
Prince of Thieves: where the PC is headed to the gallows or the chopping block, but rescued in some sort of public venue.
The Shawshank Gobbo': for the more serious Great Escape, with like a tunnel at the ready, and maybe exposing some local corruption along the way.
The Count of Monte Monteron: another tunneler, but this time with a like a personal revenge angle and a map marked with an X.
High Noon: where the prisoner transfer is interrupted by a vigilante mob, and the PCs duck out at a clutch moment.
Build a Bridge out of Her: just doing something similar to the above, but involving witchcraft
O Brother: the chain gang dash into the woods
Piranha Alcatraz: swimming to freedom, but like with the threat of hypothermia and being eaten by fish people. Maybe a shitty raft
Beastmaster: with some kind of friendly ferriet, just getting it done with the cuteness
I agree, its pretty niche and maybe falls outside what they want to do with their game, but especially for the rogue/thief archetype, having content like that would be fun at times I'd think. I'd be more inclined I think to play as a Thief and do some pocket picking or a few casual B&Es, if it maybe opened up some storyline options. Or you know, where the main downside to failing was just a fine or a short timesink to get out of jail, instead of you turning the entire town hostile like insta-murder fest
