Pickpocket Everyone In Skyrim, Even If You Keep Getting Arrested

The Pickpocket skill icon from Skyrim placed in front of a view of the game's night sky, showing two moons and an aurora borealis.


Out of all the skills available in Skyrim, Pickpocket is the most underappreciated despite its usefulness. Although it may not be as obviously impactful as weapon or magic skills, it provides a fair amount of utility for players looking for extra gold. Pickpocket can be a highly useful part of a character’s build with proper investment put into it.


Pickpocket is one of the thief skills in Skyrim, which rewards stealthy players who love to employ trickery both in and out of combat. Most thief skills have apparent benefits that players can immediately find use in. Lockpicking makes it easier to open doors and chests, offering more options for loot and exploring. Speech lowers prices at shops while making the Dragonborn better at navigating speech checks in dialogue. Alchemy allows players to brew potions with powerful effects. Sneak, of course, is the greatest skill for those looking to join Skyrim‘s Thieves Guild, allowing them to act undetected. While Pickpocket may not sound flashy, it can bring equally valuable dividends.

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Pickpocketing In Skyrim Is A Good Way To Add To The Dragonborn’s Wealth

A hooded Skyrim character talking to two NPCs in the streets of Riften.

Pickpocketing in Skyrim is a rather simple task to perform. If the player is crouching to enter stealth mode, then rather than talking to people, they will have the option to pickpocket them. The player will see a list of the items that the character has on their person, as well as their weight-value, and how likely the theft attempt is to succeed. Once the player chooses an item, they will remain in the Pickpocket menu if they are successful, but immediately forced out if they fail.

The advantages of pickpocketing are exactly what one would expect. The player can grab some extra gold or items from any character that they come across, with some characters carrying more valuable things than one may expect. Although not as lucrative as Skyrim‘s easily accessible Transmute spell, pickpocketing can give the player a welcome boost of gold. In addition, the further the player improves their Pickpocket skill, their chances of stealing successfully will rise significantly. However, one must keep in mind that pickpocketing is illegal in Skyrim, so players need to make sure that they are undetected while doing so. If the player isn’t careful, the Dragonborn could easily end up with a bounty on their head.

A thief in Skyrim should be expected to have some experience in Pickpocket, and it wouldn’t take much experimenting to see why. Stealing a few trinkets on their way through the town not only gives the player more items and spending money, but it can make them feel like a truly skilled thief. Although pickpocketing requires a little more setup than typical thievery, it is no less rewarding, especially after one sells their stolen items in Skyrim.

Skyrim’s Pickpocketing Skill Can Be Difficult To Master

A guard standing next to a jail cell door in Skyrim's Bulwark Jail.

Although pickpocketing in Skyrim is undoubtedly a good tool in a thief’s repertoire, it’s also one that players can easily end up not using. Even dedicated thief players can end up never leveling up their Pickpocket tree during the game despite it being a perfect fit thematically. Although that may sound paradoxical, there is a good reason for this phenomenon. Out of all the skill trees in the game, Pickpocket is one of the most difficult to advance through.

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Outside of skill books and paid trainers, players need to make successful pickpocketing attempts in order to gain experience in the skill. Since the chance to steal successfully for characters with little skill is quite low, this can make attempting to level the skill early incredibly frustrating. Before taking perks to increase pickpocketing chance, players will likely only be able to semi-reliably steal small handfuls of gold or tiny items. Leveling up the Pickpocket skill in Skyrim is harder early on compared to other skills, making it less approachable in comparison.

Pickpocket is a skill that players can easily pass up due to how hard it can be before the player starts to invest in it. It’s a shame when it happens, because players who can put pickpocketing to good use have a good source of income that can work for them throughout the game. While the early levels can be difficult, those who persevere can have plenty of fun with the skill.

Pickpocket Perks In Skyrim Can Be A Lot Of Fun To Play With

Art from The Elder Scrolls Online showing three characters plundering treasure chests in a crypt, while a magical foe appears through a portal behind them.

Every skill in Skyrim has plenty of perks to offer as one levels through their skill tree, and Pickpocket is no exception. In addition to stat boosts, these perks offer new bonuses and abilities for the Dragonborn once unlocked, some of which open whole new avenues of gameplay, even during Skyrim‘s best side quests. When it comes to the bonus feats one can pick up through the pickpocketing tree, players can find some of the most fun abilities in the game.

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One ability, Poisoner, lets players inflict the effects of a poison on an enemy by reverse pickpocketing it onto them. While not as effective as reverse pickpocketing grenades in Fallout, it can be a useful tool, especially with paralysis poisons. More directly useful is Misdirection, which lets players pickpocket an enemy’s equipped weapon, potentially disarming them before a fight even begins. One step further is Perfect Touch, which lets players pickpocket any equipped item, including armor. Combining this with Shadow Warrior from the Sneak tree lets players disarm and remove the armor of enemies mid-battle, giving Pickpocket masters an incredible combat advantage.

The best perks of the Pickpocket tree can turn a Dragonborn thief into a master of impossible heists. The best thief builds in Skyrim should showcase the ability to steal practically anything at will, from collecting swords from guards on patrol to stealing a bandit’s clothes right off their back. The Dragonborn is supposed to be a character with a mythological reputation, so it only makes sense for them to potentially be the greatest thief in Skyrim.

More Skyrim players should give Pickpocket a chance if they haven’t made a build featuring it in the past. While the early phase may be difficult, once the player builds up the skill, it proves to be worth all the time and effort invested. Any player with even a passing interest in turning the Dragonborn into a master thief should give pickpocketing a try the next time they play Skyrim.

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