So I got around to playing a thief and this is my experience with prison:

Pickpocket a guard, get his key. Open cell door, but hear a guard coming, close cell door. Guard goes into obvious "I'm now a hostile NPC" mode, and just opens the cell door, runs into my cell and kills me, no dialogue. Not much I could do being completely unarmored and weaponless, and trapped in a small area.

If you get caught pickpocketing a key, same thing, no chance to yield, a guard just comes in and two shots you.

So much for being a thief, having a sensible system for breaking out of prison was obviously not high on their list of things to do. I guess I stick to my usual do-gooder characters because the prison system is a joke. Having a functioning way to yield and take a longer sentence, getting moved to a cell with a master lock, etc. would've been nice.

Little else to say but "I agree". I mean, escaping from a prison is fun, but only as long as it goes as planned. The moment something goes wrong, it's not fun anymore - it's just stupid. And not because I don't like failing, it's because failing results in such stupid consequences. The aforementioned improvements would indeed be great - extended sentence and/or elevated lock level.

Are you complaining about being killed trying to escape prison and failing?

Getting killed is not the point here. I for one find it pretty dumb that when you open the door, even if the guard doesn't see it, he will become hostile the first time he sees you after that, even if you're still in your cell behind a closed door. And it'd be pretty cool to have a chance to yield, even just once, and then get a second chance to serve an extended sentence in prison, behind a tougher lock, maybe. If you try to escape again, then maybe they could beat the living hell out of you. I just think it'd be a pretty sensible improvement.

You think he didn't hear the cell close and noticed his key was gone. Oh look his cell is unlocked too. I mean really. Try and escape prison in rl and get caught... I bet they won't be asking many questions

I'm complaining that the guard AI is nonsensical and that yielding is broken.

And that it's more effective to simply sprint out of prison than try to do it stealthily.

I've tried different tactics and sprinting out of prison is 100% effective while being careful and stealthy will result in death ~60% of the time because guards are psychic and hostile once you open that cell door, even if they didn't see you do it.

Those LOOSE GRATES sure come in handy.

Also, don't get caught, and you don't go to prison. I've been to prison once one my thief character, and busted out through a loose grate. So, there's not much else I can say on it,

Not all prisons have these.

Loose grate?

I had assumed that, but I wasn't sure. Like I said, I have only been to a legit prison once, and I escaped easily through the grate.

Maybe it's best to pay the court a fine, or serve your sentence?

Some prisons have an alternate escape route, in the form of a grate you can pick and open, and escape the prison through a sewer system.

Do you even get any armor back if you do that?:/

Pay fine, serve sentence, or just sprint out. Sprinting out works pretty much 100% of the time for me. Don't have to succeed in pickpocketing a guard or picking any locks, just make them hostile so they open your cell door for you, then you dodge an attack and run out the door. But it's kind of stupid and doesn't feel very thief-like.

Your armor, and your stolen goods, are kept in two chests. You can return to pick the locks on the chests later and get everything back.

You usually get to a small window where you can pick the chest with your armor while your in the sewer.

Have you only been to the Whiterun prison?

How can you say "usually" when you've only been to a single prison?

Yeah, it's pretty bad. I once got arrested just to see what it was like to escape. I escaped the Whiterun prison by picking the loose grate and going through the sewers. From there, I was able to literally just walk right back into the prison, past the guards who just said "wait, I know you..." and didn't do anything, and pickpocket a guard to take his key. I then walked up to the personal belongings and evidence chests, took everything back, and walked out the front door a free man. I never even leveled up Sneak or Pickpocket.

You know, I guess there's a silver lining, this'd be one situation in which alteration armor spells could potentially be useful.

I prefer another alternative: don't get caught.

It's fun to go to prison now and then. Also, it's not fun to escape through a loose grate.

Two words: Winterhold Prison: if you escape that without being seen, you're a pro (but to even things out they let you keep your gear... strange)

Yeah I was probably hoping for too much. I was thinking it'd be more interesting process, but basically you may as well just serve time since it's so easy to return and steal back your things.