Pickpocketing is the second ability under the Nasty Deeds category. It allows you to steal items from merchants and other NPCs.
To pickpocket anyone you need at least 1 point in the ability. Higher level targets will require a higher skill in pickpocketing. Any one target can only be pickpocketed from ONCE during the entire game. If, however, you check his inventory and decide to steal nothing, you can come back to pickpocket him later. Even after pickpocketing your target, you will be able to target him again with another character, provided they have a high enough Pickpocketing skill.
Items that can be pickpocketed are limited based on their gold value and weight.
Pickpocketing is available only when you are in "Sneaking" mode. A hand will appear when you hover over an NPC. A red hand indicates that your skill is not high enough to pickpocket the target while a green hand signals the all clear..
Clicking on the target will bring up the inventory of items you can steal. There are 2 bars at the top of this inventory that tell you the maximum value and weight of the items that you can steal for your level. The bars fill up when you get closer to the limit.
Items that appear darker in color exceed the value or weight you have left to steal. Attempting to steal them anyway will result in getting caught and attitude penalties from the NPC, making it more expensive to trade with them in the future.
Magical items and armor appear as "Unidentified" which is great since it reduces their "pickpocket value" from their actual price. Barter with a merchant beforehand to see his stock and remember the items you want from their respective names.
Ability Level Edit
Each point you spend on pickpocketing increases the weight and value limitations on the items you can steal. However, the weight limit is capped to 5.00 at a pickpocketing skill level of 5 and beyond. The value limit increases by 200 Gold with every point.
Level 1 - 160 Gold, 0.25 Weight
Level 2 - 360Gold, 0.50 Weight
Level 3 - 560 Gold, 1.00 Weight
Level 4 - 760 Gold, 2.5 Weight
Level 5 - 960 Gold, 5.0 Weight
Level 6 - 1160 Gold, 5.0 Weight
Level 7 - 1360 Gold, 5.0 Weight
You can find Boots, Bracers, Gloves, Rings, and Necklaces throughout the game that will enhance your pickpocketing skill. You can also gain+1 Pickpocketing from the Renegade Trait (e.g. with the fish thief choices early in the game).
Notes: If you find pickpocketing skill in gear other than boots, bracers, and gloves, please add it to the list.