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.''

Pickpocket is a skill in The Elder Scrolls V: Skyrim. Pickpocket is one of the 18 skills and 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 an object will alert the Guards.

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 NPC's 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. There is also a bug related to the percentage chance near this cap. See Bugs section below for details.
 * Governing Guardian Stone: The Thief

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

"Un-stealing" Items
It is rumored that planting (or "Reverse Pickpocketing") a stolen item on an person/enemy, killing them, and then looting the item off their body removes the stolen tag from the item. This does NOT work. The stolen tag will not appear on the item while it is in the enemy's inventory, but it will reappear once the item is in your inventory.

The only way to remove the stolen tag from an item is to sell it 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.

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

Training

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

Leveling Techniques

 * An easy and effective way to level your pickpocket skill is to be jailed in the Riften jail. Across from your cell is an NPC named Sibbi Black-Briar. Unlock your cell and travel directly across to his. 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. (This no longer works, the patroling guard will attack you and when Sibbi catches you you can no longer pick pocket him, checked on PC. Still works on PS3)
 * Demonstration of leveling pickpocket skill easily in the Riften jail. (youtube)
 * When taking and trading items, put in around 300 gold and take back that gold. This is much more effective than stealing items because pickpocketing gold gives you more XP.
 * Another easy way is to find a guard, pickpocketing all his gold, and put back a small amount of gold (100-200), pickpocket your money back and repeat.
 * You can also train your Illusion skill and a skill of your choosing when your training pickpocket. First you have to buy the spell Muffle. Then you go to a skill trainer of your choice and ask him/her to train you in that skill. Only ask to be trained once and then use Muffle. After that, pickpocket your money back and repeat. It is recommended to save after each pickpocket as there is a chance pickpocketing your money back may fail.

Bugs

 * When pickpocketing any item from someone and are close to the point where the item becomes 0% chance to steal or the maximum cap for stealing Gold (based on your Skill points and increased by Cutpurse Perk), any equipment giving you additional Pickpocketing success will actually degrade your success percentage.
 * Example: If you are at a skill level appropriate to steal up to 1500 gold, when you attempt to lift 1400 you will actually have a lower chance of succeeding if you have any equipment that enhances pickpocketing rates. The reason seems to be the way the enchantment is added to your success chance: the curve makes these bonuses more effective for stealing low amounts of gold/quality of items than high amount and quality. However, near the apex of difficulty these bonuses are actually falling below 0% additional effect, negative effects increasing the closer to value cap.
 * If target is actually standing up from paralysys you can pickpocket everything from him (even big amount of money) without being noticed. But it won't be counted to your pickpocket level.

The Elder Scrolls V: Skyrim Skills
See: Skill (Skyrim)