Just wondering who has actually gone to jail, and what it's like. I remember Todd saying each jail is unique, but have never gone to one yet. It's to my understanding that it lowers your leveling bar. Not 100% sure what the effect of that is.

well i was only in winterhold jail. You are basically in a cave, locked in a cage that is guarded from a frost atronach. if you managed to get out of that cave you are getting attacked from like one million frost atronachs and horkers

Just in Markarth, as part of a quest line.

Riften holds prison is very normal. What you'd expect a jail to be. Thus, there's definitely difference between these two jails.

I like riften's prison.

It's very warm and cozy.

Well, for a prison.

I was really suprised at winterhold jail but after some thought i should have known it seeing that the college has their seat there and winterhold only having having four houses

I think the only prison I haven't been in is the one in Windhelm since, I don't often go there.

Besides that, I have been in all prisons across Skyrim.

Heck, even prisons that aren't in any cities.

And also (most) jails have epic escape routes.