Jail Break (Skyrim)

This is a quick guide to escaping out of all the jails' prisons in all the nine holds of  and the island of Solstheim. This guide will cover the multiple methods of escaping prisons including: the most direct ways of escape, alternate escape routes and secret passageways in short detail.
==Major cities (with keeps)==
===Markarth===
See No One Escapes Cidhna Mine article. Basic walkthrough: Ask anyone who Madanach is and follow the questline.
After completing the mission "No One Escapes Cidhna Mine" it is impossible to ever get out without serving time. (However, there is a bug in which the Dragonborn can trap themselves in Cidhna Mine forever by hitting the ore with a pickaxe, they can deplete the silver veins and since the ore does not reset after a certain amount of time; they will never be able to get the option to serve time. See the Cidhna Mine article for a fix to this bug.)  
One possible way, however, is to kill Madanach and Borkul within the main area of the mine. Both of their bodies are permanent, and their keys can be stashed on them for future use. 
===Riften===
The Dragonborn starts off in what looks more like an ill-treated hotel room than a cell. To the right there is a desk with a lockpick hidden amongst the food. Behind is the bed, and to the left is a dresser and a bucket. If they notice on the back wall, there is a shackle. Activate it and it will move the wall; revealing a tunnel. Enter them, and keep moving through the tunnels (sometimes when activating the shackle; the wall will stay up but the guards will turn hostile and attack). Eventually there will be a sewer grate, open it and there sits the Dragonborn's confiscated items. Travel through the sewers until there is an exit. This does not work on the Xbox as of patch 1.6.
Firstly pick the lock of your jail cell or pickpocket it off the guard who will be standing next to the cell when the Dragonborn is jailed. Sneak towards the passageway to the left, then enter a door on the left hand side (not in front). Turn left, enter another door, and there will the confiscated belongings chest in the top right hand corner.
Exit out the same way but turn right and go through the door seen when entering the passageway. Head up the steps, turn right and there will be the door leading out to Riften.
===Solitude===
Solitude is perhaps the hardest of the jails to escape.
First, after being jailed, in the cell under a bucket in the corner on the left side of the door there is a lockpick which is very useful if the Dragonborn's breaks, turn and check the wall on the left side of the windows towards the bottom. It should say "Activate Crumbling Mortar." After activating it, the wall will crumble. Follow the path and they will be brought to a hole in the wall from which one can access the Prisoner's Possessions box, which has an adept lock. The key can be looted off the guards once they have been killed, or alternatively, pickpocket the key. Be careful to wait, as guards will come through the crumbling wall and exit through the Dragonborn's prison door, leaving it wide open. Do not go that way though. If the Dragonborn has a high Sneak skill, just step by the hay pile and let them go through (there are two guards.)
Then, take a right, around the corner, and head for the manhole exit. It will exit onto on a platform of land behind a house. Jump down from the ledge to be free. If there is no option to activate the crumbling wall, the player can also phase through the wall very easily using the wooden plate on the table.
Escaping without using secret passages is much more difficult. Unfortunately, the steps are too complicated to mention, due to guards being everywhere, but there are a few basic things to have. Firstly, the Dragonborn will need to have a good level of magic, and must be able to cast Detect Life and Muffle (Invisibility also works).
To escape, the basic route is to escape the jail cell, walk to the passageway directly ahead, follow the path up the steps, turn first left, down the steps, and the belongings chest will be on a table. Follow the path onwards and eventually reach the door into Castle Dour, and then Solitude.
The Dragonborn can also wait for the guard to patrol around and pickpocket the jail key from the guard to unlock all the cells or just their own. The key can also be used to take their belongings from the chest rather than picking the lock.
===Whiterun===
Once a crime is committed in Whiterun and the guards catch the criminal, they can choose to end up in the Dragonsreach Dungeon.
Once the Dragonborn is inside their cell, they are stripped of all items except for one lockpick. There are two possible ways to escape from the prison. The first one is shorter but much riskier. When out of sight of any guards, pick the lock to the main door of the cell (an adept level lock). Then reclaim any confiscated equipment from the evidence chest.
Any belongings can be found in the evidence chest, but a guard patrols the area the chest is held in. Once the equipment is retrieved, the Dragonborn must carefully escape through the main door, because there are several guards patrolling there as well.
The other way of escaping is longer and safer, but it is still not that easy. In the cell, there will be a dead bandit lying on the ground. The bandit will be lying on top of a sewer grate with a novice level Lock. Open it and drop into the sewers.
While progressing, there should be a set of stairs leading to a hole in the wall. Through the hole, the lock on the evidence and prisoner belongings chest can be picked to retrieve any confiscated equipment. Deeper into the dungeon, there will be an exit into the guard barracks. Exit the sewers to safety.
Note: Proceed with caution as the guards may become hostile after the jailbreak.
Another way is much more action worthy. Equip the spell Sparks and wait for a guard to come by and attack them with Sparks. Continue attacking until the guards become hostile. They will unlock and open the cell door, allowing an alternate escape route for the prisoner (try to get confiscated equipment first before escaping).
===Windhelm===
Escaping Windhelm prison is quite difficult, and a high Sneak skill is recommended.
To breakout, the prisoner needs to pick the lock of their jail cell. There is only one exit, so head up the path and up the stairs. There will be a fork in the hall, so just head out of the keep.
===Raven Rock (Dragonborn DLC)===
Escaping the Bulwark prison is quite easy, as even low level thieves can escape without alerting the guards.
To escape, look under the firewood of the fireplace. Unlock the novice level grate and drop down. Run to the right and head to the edge of the walkway. Unlock the prisoner belongings chest to retrieve confiscated belongings and then drop down again. Continue through the sewers until there is a door to Coldcinder Cave. Enter the medium-sized cave (there are skeevers and a few Netch here, which help for the quest to find Netch Jelly for the Raven Rock alchemist.) and walk out into Solstheim.
==Other cities (without keeps)==
===Dawnstar===
The jail layout of Dawnstar is the same as Falkreath.
First, as with most cities, the Dragonborn will start in a cell with one lockpick. Be careful when picking the lock because once the lock is picked, the guard will know and come over to the cell. The key can also be pickpocketed off of the guard.
Note that in the back right corner of the cell there is the lockpicking skill book The Wolf Queen, Book I.
An easier way is to shout at the wall. The guard will come over, asking to stop shouting and leave the door open. Also, if the Dragonborn leaves the cell, the guards will not be hostile.
Once out of the cell, turn left to find a desk and the evidence and belongings chests which contain all confiscated equipment. The key can be stolen off the desk or lockpick the chests to get the belongings back.
The exit out of jail is right in front of the cell.
The key to the jail is on the table where the prison guard sits. The key can be taken by using the Telekinesis spell to bring it over to you.
===Falkreath===
The jail layout of Falkreath is the same as Dawnstar.
First, as with most cities, the Dragonborn will start in a cell with one lockpick. Be careful when picking the lock because once the lock is picked, the guard will know and come over to the cell. The key can also be pickpocketed off of the guard.
A second, much better way is to shout at the wall. The guard will come over, asking to stop shouting and leave the door open. Also, if the Dragonborn leaves the cell, the guards will not be hostile.
Once out of the cell, turn left to find a desk and the evidence and belongings chests which contain all confiscated equipment. The key can be stolen off the desk or lockpick the chests to get the belongings back.
The exit out of jail is right in front of the cell.
===Morthal===
The jail layout of Morthal is similar to Dawnstar and Falkreath.
As always, the Dragonborn starts with one lockpick. Either pick the lock or shout at the wall, the guard will come over and request to stop, walking away without locking the door.
Be careful when opening the cell door as the guard will come over. Hide in the opposite corner of the bed and he will not notice. Proceed to either sneak around or kill the guard.
Confiscated belongings will be in a chest just a little in front of the cell. One can walk out a little, and find a barrel with three extra lockpicks to help in picking the chest lock.
The exit is in front of the cell door. There are four guards on duty here, and escape is almost impossible unless the Dragonborn has a high sneak skill or casts a Muffle or Invisibility spell.
Alternatively, use Whirlwind Sprint at the wall to go through it and spawn next to the door, but do not forget any confiscated items. This may not work every time (tested only on Xbox 360).
===Winterhold===
The Chill is rather unique as the Dragonborn retains all of their items, even the stolen goods. This is probably the easiest jail to escape from, especially if going for the "Wanted" achievement after acquiring enough bounty in all nine holds for the "Master Criminal" achievement and paying it off in the other holds.
First off, after being arrested the Dragonborn is transported very far north, past Septimus Signus's Outpost. They will be in a small cage with one Frost Atronach acting as a guard. Kill it using shouts if at a low level, or open the gate and battle it, or use the spell Flames on it from inside the cage (it will not attack if it is killed in this way). Note: spells other than Flames, Sparks, Frostbite, Arniel's Convection, or Vampiric Drain will impact on the cage walls (i.e. concentration spells).
The cage itself is an adept lock so, before being jailed, bring lockpicks. Outside are three other frost atronachs and there is a chance to see a Sabre Cat or Horker depending on the level.
To escape, just turn around and run up the small mountain onto an ore vein. The enemies will not follow and will eventually give up, allowing the ability to fast travel away.
However, if the Dragonborn is not yet strong enough to fight Frost Atronachs, the simplest thing to do, since they have all of their inventory, is to pick the lock and sprint out of the cave and into the ocean, where the atronachs will not try to fight.
==Tips==
*If planning to go in jail on purpose, an escape can be made easier even before getting arrested; get in the Guard Barracks and drop lockpicks or anything desired before each cell door.
**As keys cannot be dropped once obtained, only stored (if the jail has a container which items can be stored in, a key can be placed inside) there is no need to try and get them before being placed in jail.
*While in jail, if the Skeleton Key was obtained during the Thieves Guild Questline, (though it may not show up in the inventory) it will be used to pick the locks instead of normal lockpicks.
*If the Lesser Power Secret Servant from the expansion is equipped, he can be used to smuggle any items into the cell, assuming it does not surpass his carry weight.
*If the Dragonborn does not have any lockpicks before being jailed one will automatically be placed in their inventory.
*If planning to go to jail on purpose, you can give everything you may need for the breakout to most followers and they will bring it to you. Lydia is one of these followers.
==Achievements==
==Bugs==
* If the player has a high bounty and is placed in the Solitude prison, the guards may be hostile even when the player is in their cell. This requires the player to sneak to the bedroll to serve their sentence, as to not stir the guards.
* Sometimes when in the Whiterun prison, belongings on the dead bandit will disappear. A way to avoid this is to place belongings on the dead skeever or a barrel in the sewers to collect. Be cautious when using barrels to store items, since they will reset to normal barrel contents after a certain period of time.
*The Riften jail's escape route marked by a Thieves Guild Shadowmark may still be bugged. A button next to the symbol will say "Activate Broken Shackle," and usually upon activation will force a wall to collapse in the back. For now, the chain that is usually there is not rendered, and the wall itself will not collapse.
Category:Skyrim: Quests