Despite being a crime-ridden country, Skyrim's penal system is rather lackluster. In fact, it enables criminals to get away with their wrongdoings.
The Elder Scrolls V: Skyrim's prison system doesn't make sense, as powerful mages are held within simple confines that don't suppress their magic. Bethesda may have long, intricate explanations as to why the political and religious institutions of the country of Skyrim are the way they are, but the lore behind its lackluster penal system is notably missing. Considering that the game is filled with bandits, assassins, and thieves who belong in jail cells, Skyrim has quite a bit of explaining to do.
The prisons in Skyrim are typically simple. Save for the Reach's, most of the game's prisons consist of a few cells and the guards who watch them. Players who are arrested will have their items - including clothing - confiscated by guards and will be placed in a cell with the only possessions left to them being rags and a singular lock pick. Players can use the latter item to break out, but even Skyrim's best lock pickers may have a difficult time escaping from the prison with their items, which are locked away in the master-level-locked Evidence Chest. Alternatively, players can serve their sentences by going to sleep on the beds in their cells and receiving all of their non-stolen items back from the guards.
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While such a description may make Skyrim's prisons sound secure, the truth of the matter is that the game's penal system is built around letting criminals get away with their crimes. Even if it is just one lock pick, the Dragonborn is given an item designed to facilitate their escape when placed in a cell. The Dragonborn can even avoid that matter altogether if they simply pay a fine upon being arrested for their wrongdoings, regardless of whether those wrongdoings consist of petty thievery or cold-blooded murder. But truthfully, the simplicity of the jail cells is the real culprit behind Skyrim's poorly managed prisons, as they stand no chance against the skillful thieves, mages, and warriors who roam across the lands of Tamriel.
Before being locked away in a prison cell, the Dragonborn first has to become a wanted criminal in whichever of Skyrim's Holds they are in. To do so, the Dragonborn must conduct illegal activities, which include stealing, lockpicking, assault, or even shapeshifting between werewolf and vampiric forms. Each of these crimes comes with a fine to match their level of severity: Trespassing will only land the Dragonborn a fine of five Gold, whereas murder will land them a fine of 1000 Gold. Nevertheless, the Dragonborn will be considered a wanted criminal as long as they have a fine attached to their name and will thus be approached by Skyrim's arrow-stricken guards who will attempt to make an arrest. However, the Dragonborn always has the option to evade arrest by simply paying the fine attached to their name.
This last aspect about Skyrim's penal system is perhaps the most confusing of them all. In many ways, the country of Skyrim is presented as a mostly impoverished one, filled with people who rely on agriculture and small shops in order to get by. The fining system could work for people who cannot afford to pay the toll, but the Dragonborn, along with the criminals of Skyrim, will almost always remain unaffected by fines. The richest people in the country of Skyrim are those born into wealth and those who are willing to cheat the system through criminal means. This includes the mafia-like Black-Briar family and Skyrim's Thieves Guild, or even the random troupes of bandits wandering through Skyrim's Holds. When presented with a possible fine, such people could easily pay off guards with stolen money or even use the influence of their criminal organizations to not pay anything at all.
Additionally, that Holds do not arrest criminals who committed crimes in other Holds is just bad policy. The country of Skyrim is experiencing a Civil War, so it is understandable that its different regions may not care for one another. However, limiting the number of potential criminals in Skyrim is in almost everyone's best interest, so keeping track of the wanted people from other regions in the country would be a smart idea that simple, inter-Hold communication could handle. Instead of doing that, though, the Holds appear to remain at odds with one another due to the Skyrim Civil War - as well as cultural differences - in turn enabling criminals to pillage the country one region at a time.
If a criminal ever enters a jail cell in Skyrim, they will be happy to find that it is as easy to escape from as is evading imprisonment in the first place. The cells in Skyrim's prisons are kept shut with an easy novice level lock that can easily be picked with either the pick given to the prisoner upon being stowed away or with one of the others in the cell the guards did not care to search for. Given that Skyrim has two criminal organizations - the Thieves Guild and the Dark Brotherhood - that specialize in stealth and breaking and entering, such a weak security system feels incredibly out of place in a country as dangerous as Skyrim.
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Additionally, the prisons make no attempt at limiting Magicka users in their cells. Skyrim is primarily a Nordic land, so it is understandable that the average guard would be more concerned with melee attackers than mages and witches who use what would be considered elvish or Breton-based means of combat. However, the College of Winterhold is still located in Skyrim, and spells can easily be cast through the bars of a prison cell. Trying to imprison a Destruction Magicka user in Skyrim is thus nearly impossible, as they can always force their way out.
This speaks to the sheer ineptitude of Skyrim's prison system. Not only does the fining system make prison the easiest to avoid for actual criminals but people locked inside a jail cell will find it incredibly easy to break out. Perhaps Bethesda kept the prisons this way to show the corruption within government bodies in the region; after all, major criminal organizations have influence over how the Holds are run. Nevertheless, the ease with which the Dragonborn can avoid punishment for their crimes feels like a major oversight in The Elder Scrolls V: Skyrim.
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