I've noticed a couple oddities with these too, although my main concern was they backlog at busy times. At the risk of asking a very basic question, are you certain you have enough staff to escort them anywhere? Is it specific to the prisoners who have been flagged as having contraband? Are your solitary cells (if relevant) functioning otherwise as there's been some issues lately with prisoners not being escorted to solitary?

One thing I can say I did have my prisoners doing, was they could get displaced onto a nearby wall and were seemingly inaccessible to be moved, altering my setup and temporarily removing walls or establishing prisoner direction zones did help at the time, but I haven't had a repeat of the problem for some months. Are they out in the open or stuck atop the checkpoint? (ie would deleting the checkpoint help?)

Sounds like a really strange issue, sorry I can only throw questions and blind trial and error suggestions at you. Fingers crossed someone else on here has experienced this closer and has a solution!

Yeah I've got like 45 available officers and a bunch of orderlies. Got all DLCs also.
The checkpoints glitches even more badly with barred walls which I like to put around water spot to incarnate the idea that characters would see the water if they were real.
Solitary cells works well, I've got a bunch of them for each grade of prisoners, and nuts. They worked well before I discovered checkpoints. Some checkpoints works well, some other produces glitches. Now after rebooting the game a few time, a few glitched characters fixed themselves, but there's still one glitches as for now. They seemingly are glitching when being intervened with, but they also glitch even worse with these walls. Removing the checkpoints and redoing the whole area changes nothing.
Now, that character that is not handled, it gets pushed around and what's awkward is to watch the guardians bounce around it all around and push it in a direction and another and always seem like "Finally!" but nope. LMAO

Drat - sounds like you've got all the obvious covered... fingers crossed this weeks bug fix might magically solve it. I was going to suggest using one of Murgh's mods to just outright delete those prisoners (probably could be done via gamefiles too, but been a while since I've messed with them) to just get the glitched ones to flip off, however I don't know if you've got mods/cheats enabled as, if not, that won't be very useful to you! If they haven't completely glitched beyond all needs though, presumably they'll starve at some point. Problem morbidly solved... or at least symptoms sort of alleviated.

Yeah I try to beat the game at itself with no cheats and right now I activated anything that could give me trouble; gangs, changing traits, nuts, random events and all sorts of stuff ha ha... It's been quiet since the beginning, a few deads, but I can let it run for a while fast forward without intervening much.

Oh, something new: Now the "To Do: Escort prisoner to solitary" is red, after a few reboots of the game. It was green, before.
Hmm.. Still nothing tho it turned yellow.
Definitively: If I cancel punishment, it still is stuck on "todo: escort to solitary"
Rebooted again, when I reboot, it's green, then a guard comes at the prisoner, then it turns red, tho, there's a prisoner of the same security level already in specific colour solitary.
Ha! I did it! I've put a solitary right under the character and suddenly, it brought a guard at it with or without direct correlation.
Later on: it's still happening with other character. Now, one mom prisoner, no shackles but still stuck with yellow "escorting to cell".
IT's also written "Store log in table" in green, but it's as if she was glitched with a worker's tasking. Workers too behaves weird lately, went from a 100 000 daily cash flow to 8k. ... Pff saying that, it went up to 270 000. But mother prisoner still stuck.

lol... And it's useless to install toilets for glitched checkpoints, characters aren't using them; they're glitched. Of course. lol

More and more are stacking on other rooms's checkpoints too. One prisoner literally was
jacked on top of a wall. Nonsensical.

now... All prisoners in the reception room are also stuck with the yellow "escort to cell". There are around 50 free guardians...

Yeah... After adding like... 3 guardians for 1 prisoner, which is around 175 guardians, it finally dejammed. What's weird is that there are tons of guardians wandering and doing nothing so IDK there's a glitch for sure, but it'S not everlasting.

Having this issue RN I'm also using a basic bug fix mods and this is still a problem in 2025 :(