There have been a couple of threads regarding pickpocketing and asking how it works with the "Loaded Pockets" Berath's Blessing. If you want information on Loaded Pockets, you can go here.
In anticipation of the new patch, I decided to do a deep dive and try to figure it out. To pickpocket an item, you need to be actively in stealth. When you activate a pick pocketable creature, you will see it's pick pocketable inventory. Items that cannot be pick pocketed are greyed out but show it's "Sleight of Hand Difficulty Level". Items that are not greyed out are items that you can pick pocket- you already have the necessary Sleight of Hand to pick pocket those items.
To pickpocket, you actually do not need any points in Sleight of Hand- but you do need to actively be hidden.
In terms of determining the Sleight of Hand Difficulty Level, there are a few modifiers. These are actually in global.gamedatabundle lines 10393-10545 and are in the spoiler below. I'll break it down below.
The first factor is if you are currently in a creatures field of vision. This is indicated with the '"eye" appearing in your selection circle while stealthed. This increases the Sleight of Hand Difficulty Level by 2.
The second factor is if you are currently detected. You are considered "detected" when the stealth meter in your selection circle is red. This increases the Sleight of Hand Difficulty Level by 2.
The third factor is the level of the creature you are pickpocketing. It is as follows:
At level 1, the difficulty increases by 1.
At level 2, the difficulty increases by 2.
At level 3, the difficulty increases by 3.
At level 5, the difficulty increases by 4.
At level 7, the difficulty increases by 5.
At level 10, the difficulty increases by 6.
At level 13, the difficulty increases by 7.
At level 16, the difficulty increases by 8.
At level 19, the difficulty increases by 9.
The fourth and last factor is the type of item you are attempting to pickpocket. They are as follows:
Weapons increase the difficulty by 2.
Armor increases the difficulty by 3.
Clothing increases the difficulty by 1.
Consumables do not affect the difficulty.
Ingredients decrease the difficulty by 1.
Quest items decrease the difficulty by 3.
"Misc" items decrease the difficulty by 3.
Any ship upgrades/crew, food or drink, and artifacts do not affect the difficulty.
Theoretically*, the highest Sleight of Hand Difficulty that a creature can have is 16. Therefore, this means that to pickpocket every creature in the game, you need 16 Sleight of Hand.
*In practicality, not very many creatures are level 19+, and fewer still are non-hostile NPCs, so that number could realistically be lower.
There appears to be two "inventories" for creatures. One that can be pickpocketed, and one that can't. When you kill an NPC, the loot they drop is from both "inventories".
It's important to note that if you get caught pickpocketing a faction NPC (and this applies to stealing from "owned" containers or opening "owned" doors, as well), you will gain minor negative reputation with that faction.
While hidden, you can also reverse-pickpocket explosives. You do not require any points in Sleight of Hand to do so. Explosives, in general, scale with your Explosives skill. When you reverse-pickpocket a bomb into the character's inventory it gains +100 Accuracy to hit and you have 10 seconds to get out of the radius before it explodes. (If you want to know how explosives work, go here)
The Sleight of Hand skill is also used in scripted interactions and conversations. Typically, the Sleight of Hand options involve misdirection and skullduggery.
There is also a game engine quirk that allows you to become completely hidden (regardless if you are being looked at/etc) while in conversation with an NPC and the game is unpaused. This means you can initiate pickpocketing to at least see the inventory of just about every major non-hostile NPC in the game.
Edited by Prince of Lies, 26 October 2018 - 11:21 PM.