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 . 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 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 .