Pickpocket

''The stealthy art of picking an unsuspecting target's pockets. A skilled pickpocket is less likely to be caught and is more likely to find valuables.'' "I find your hand in my pocket, I'm going to cut it off."

- Guard

Pickpocket is a skill in and is one of the six skills that falls under The Thief play-style. The intent of the pickpocket skill is to provide greater role play opportunities and much more realistic thievery. The player is free to peruse their target's inventory, without breaking the law. Unsuccessfully removing or adding an object will raise the Dragonborn's bounty.

There are many opportunities for lucrative pickpocketing to offset the significant costs of investing perks in the skill. Many NPCs will carry large amounts of gold and/or valuable jewelry that is frequently enchanted. Gold from training or bribes will also be in the NPCs inventory which can then be stolen with the pickpocket skill.

There is an unknown formula for maximum gold value that can be pickpocketed based on the level of the character's pickpocket skill and which perks they have. This can result in situations where even a small change in gold value can result in huge swings in percentage chance of success.
 * Governing Guardian Stone: The Thief

Perks
The following are the perks that become available to select as the skill is leveled up

Books
The following books increase this skill:
 * Thief
 * Aevar Stone-Singer
 * Guide to Better Thieving
 * Beggar
 * Purloined Shadows

Trainers

 * Ahkari (Adept): Khajiit Caravans
 * Silda the Unseen (Expert): Windhelm
 * Vipir the Fleet (Master): Thieves Guild in Riften

Leveling Techniques

 * The best method, should you be looking to avoid potential NPC deaths, is to loot from city guards. This allows you to continually find something to pickpocket, and it allows you to instantly get caught upon failure (avoiding any potential deaths of aggressive NPCs resulting from a failed pickpocket).
 * An effective method to level this skill is to become Guild Master of the Thieves Guild. This allows for you to steal from any guild member without causing any major action on the NPC's part (ie. no bounty or combat is caused upon failure). Now, here is how best to go about looting the guild members:
 * 1. Loot every member of the thieves guild
 * 2. Wait for 24 hours in either the Cistern or The Ragged Flagon
 * 3. Change to the location that you DID NOT just wait in
 * 4. Loot every member in JUST THIS location
 * 5. Wait another 24 hours in the area you are currently in
 * 6. Repeat steps 3 - 5 as many times as needed to completely loot every member


 * NOTE: It is not certain if, or when, NPC's inventories will reset. The above method could be repeated as many times as feasible should the guild members gain more items to pickpocket.

NOTE: This has been corrected with the new update. There is now a 0% chance to steal back the gold if you trained five times in a row.
 * Simple and effective method is to quicksave before each attempted pickpocket. If successful, save again, if unsuccessful, re-load. Inns and marketplaces are good places for pickpocketing as there are many NPCs there and you can/should pickpocket them one by one and then move to the next marketplace/Inn. Also, to increase your chance of success, only pickpocket 1 item at a time. For example, find someone, take a small item, exit their inventory, and re-pickpocket them.
 * The quickest way to do above is to find any of the trainers in this skill and have them train it as much as you can, then pickpocket the gold off of them. Each time you do this, especailly in the lower levels, you should level up, allowing you to do this an unlimited number of times at a time. Make sure to save before and after each attempt, in case you get caught.
 * An easy and effective way to level your pickpocket skill is to go to the Riften jail.There is an NPC named Sibbi Black-Briar in a cell. Through the bars you may pickpocket him freely. Even if he catches you, he will allow you to continue and raise no bounty or attract any attention. After pickpocketing him of his belongings you can place the stuff back on him and repeat the process indefinitely. Additional Note: Tested in Patch 1.4, no longer working.
 * Use Calm spells on normally hostile enemies such as Bandits. As long as Calm is still affecting the enemy, you can pickpocket them, and even if you're caught, they won't attack you.
 * If you don't mind increasing your lifetime bounty, complete the city influence quests and pickpocket anyone you feel like with impunity. If you get caught, just tell the guard that "you're with the thieves guild" and you'll be able to pickpocket again. This tactic results in a 12 gold fine each time you get caught but you can increase your skill very quickly using the Thief Stone.
 * The chance of successfully pickpocketing an item is put into a percentage at the bottom of weight and value(with the light fingers perk).
 * As Guild Master in the Thieves Guild, you can also pickpocket any of the member freely. When you get caught, they would say "You could've just asked", but then you will be unable to pickpocket from them again and you will get the message "xxx has already caught you".

Removing 'Stolen' Tag
To remove the 'stolen' tag from items: get a follower, drop the stolen items and get them to pick the items up. This usually removes the 'stolen' tag from the item but if not the process can be repeated. CAUTION: Do not drop items in groups of multiples, drop one at a time or there will only be one of that particular item in your followers inventory. eg. dropping 7 Ancient Nord War Axes will result in just one Axe appearing put hovering over it will reveal (7) Ancient Nord War Axes. You will only recieve one axe back from your follower. You can also store items in a container (chest or sack) in a home you own, then order your follower to 'take all' items from the container. CAUTION: Do not place items that do not have the 'stolen' tag into the container as upon taking them back from your follower they will have the 'stolen' tag newly attached to them.

Another, more expensive way is to sell the item to a Fence and then buy it back at a much higher price. Speech perks can be used to reduce the cost of buying back the item. Additionally, you can use the Fence perk from the Speech skill to use any merchant whom you have Bartered with as a Fence. (Patch 1.4 on PS3 disables this method as well as using a follower)

A method found 08/04/12(patch 1.5), on PS3, even more expensive than the other 2 patched methods. Putting the item you wish to remove the stolen flag from into a merchant shop's inventory, then buying it from the merchant. eg, waiting for the merchant caravans to arrive at Dawnstar(making sure their inventory will not refresh after speaking with them), then going to the invisible Dawnstar chest, and putting the stolen item inside that chest. Then buying the item from the merchant like any other item.(confirmation required)

Trivia

 * The chance to successfully pickpocket any item (including gold) is capped at 90%.
 * The value and weight of an item determines the difficulty of pickpocketing the item.
 * It is not necessary to be completely 'hidden' to successfully pickpocket, though it does raise the chance to steal items significantly. It is, however, necessary when pickpocketing equipped items or weapons.
 * After unsuccessfully attempting to pickpocket an NPC, the NPC cannot be pickepocketed again for 2 days. The NPC will not reset if the player waits two days in the same room.
 * With the Poisoned perk, placing a paralyzing poison on a target will allow you to steal any item.
 * If you can successfully pickpocket a Forsworn Briarheart, and steal the Briar Heart from his inventory, you will kill him.
 * It is possible to pickpocket items with 0% chance to steal. However, it is required that you have the Poisoned Perk. Simply get any type of paralysis poison, place it in the target's inventory and while he is down pickpocket the desired item. (Confirmed on PS3)
 * The above method will also work if you have a Staff of Paralysis but will only work on some NPCs others will possibly become hostile (Confirmed on Xbox 360)
 * A good way to raise the pickpocket skill is to steal an expensive item from a merchent/sell it back and repeat
 * The Perfect Touch perk does not work on essential NPCs.

Bugs

 * Enchantments that boost pickpocketing chances actually reduce your success rate when your base chance is small. (Such enchantments grow less effective as the value of the item being pickpocketed increases; for the most difficult items, these bonuses fall below 0%, giving you a negative "bonus").
 * If target is standing up from paralysis, you can pickpocket everything from them without being noticed. However, this will not increase your pickpocket level.