Through one deed or another, I have found myself in Riften jail. How I got there is not it important (I stole someone's sweet roll DX). Me, being the master criminal I am, have found myself in many-a-cell, and through cunning wit alone, I have evaded serving an actual sentence. I will not let Riften stop my streak! The worst part of it all, is that taunting shadowmark. The shadowmark is the symbol for a way out, and beside it, on the wall, is an invisible broken shackel. When I activate said shackel, absolutely nothing happens, and the "activate" promt disappears. Tell me, my internet palls; "How do you escape Riften jail?"
How to escape the Riften jail
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This is done in three parts:
Part 1: Get into the good graces of the Jarl
How you do this is dependent on who controls the city during the Civil war:
If you don't let the Imperials take control of the city, the Jarl will be Laila Law-Giver. You can win her favor by completing all parts of the miscellaneous objectives that starts with Wujeeta at the Fishery.
If the Imperials have taken control, you can win favor with the newly installed Jarl by speaking to them.
Part 2: Become a champion of the people of Riften
Once the Jarl likes you, you'll be able to secure her trust by helping the people of Riften. Completing five miscellaneous objectives or favors in Riften will complete this step.
Part 3: Handle Riften's drug problem
There are three miscellaneous objectives you need to complete: "Helping Hand", "The Raid", and "Supply and Demand". You might've already completed these as part of the first two steps.
Once complete, you can purchase your new home for a cool 8,000 gold.
For a complete walkthrough, this is exactly what I did:
- Spoke to Wujeeta and completed "Helping Hand" by giving her a healing potion.
- Intimidated Wujeeta into telling me where she got her Skooma
- Spoke to Jarl Laila in Mistveil Keep and told her who the dealer is, and accepted her request to shut him down
- Went into the Riften Warehouse, confronted the dealer, and retrieved the information about where the Skooma was coming from
- Told the Jarl about the source, who then told me to deal with it (noting that I'd be well on my way to a title in Riften for doing so)
- Went north to Craigslane Cavern and disrupted the Skooma operation by killing everyone inside and outside
- Reported back to the Jarl about the disruption. At this point, the Jarl didn't have anything new to say.
- Spoke to Wylandriah, the Jarl's mage, and completed her retrieval quests by going to Windhelm, Winterhold, and Ivarstead.
- Spoke to Sibbi Black-Briar in the Riften jail, and subsequently completed "The Lovers Requital"
- Completed a dragon bounty given by the Jarl's steward.
- Spoke to Romlyn Dreth and subsequently completed "Under the Table."
At this point, I received a new objective to speak to the Jarl. Upon speaking to her, she said she'd make me Thane once I purchased a house in Riften, which I was then allowed to do by speaking to the Steward.
Thieves caches are located all over Skyrim. The Riften cache is located in the garden of the house you can buy there. In the back of the garden you should find there are some barrels, one of which is the Thief Cache appropriately named "Thief Cache" :)
The house is located at number 7 (top-left) on the map below if you don't know where it is.
Also keep a look out for this "shadow-mark", it's means there is a thieves cache somewhere nearby.
You can learn more about the Thieves Guild shadow-marks here.
Best Answer
There are two ways to do this but they both start the same way. Pick the lock, sneak behind the guard in the room on the left, get your stuff. Now you can either
HOWEVER, you may not want to leave this jail so quickly. It has a bug that allows you to easily level up your pickpocket skill to 100.