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 one of the 18 skills in The Elder Scrolls V: Skyrim and falls under The Thief. It includes a robust set of perks that affect different aspects of pickpocketing and can even be combined with poisons from Alchemy to attack with the proper perk. Pickpocketing requires the character to be Sneaking, but not necessarily hidden, to Pickpocket. Opening the pickpocket menu is not illegal but an unsuccessful pickpocket attempt will be reported as a crime, alerting any nearby 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.

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

Pickpocket 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

A easy way to train pickpocketing is to pickpocket the money that you spend on training back from their pocket.(Effective only until level 51 in the skill that you are training).

Bugs

 * BUGGED: When pickpocketing gold from someone, when you are close to the Maximum Cap for stealing Gold (cap based on your Skill points and increased by Cutpurse Perk), any equipment giving you additional Pickpocketing success will actually degrade your % chance to steal it. Example: If you are at a skill level appropriate to steal up to 1500 gold, when you attempt to lift 1400 you will have a lower chance of succeeding with any equipment on that enhances pickpocketing skill. The reason seems to be the way bonus skill from equipment is added to your success chance: the curve makes these bonuses more effective for stealing low amounts of gold / quality of items then high amount / quality, however, near the apex of difficulty these bonuses are actually falling below 0% additional effect, negative effects increasing the closer to value cap.