Pickpocketing

Characters can be pickpocketed while sneaking and hidden using the "activate" function while facing them. This will open the inventories of both the player character and the target. Items can be transferred either way, and thus items can also be planted on them, also known as reverse-pickpocketing.

Characteristics
If detected, the non-player character will automatically reclaim the item(s) taken and the player character will not be able to pickpocket that non-player character again (at least not straight away - leaving the area and returning 24 hours later should allow the player character to re-attempt this).

The player character cannot steal items a non-player character currently has equipped. To steal an item the non-player character is wearing or using (armor or weapon), the player character can reverse-pickpocket a better item (higher DR for armor, higher damage value for weapons) into their inventory and then leave and re-enter the area. The non-player character will equip the item with the highest stats and then the player character may try to steal the item they were using before.

Formula
Pickpocket Chance is rounded down to an integer. It cannot go below fPickPocketMinChance or above fPickPocketMaxChance. For each item the player character steals or plants in a non-player character's inventory, there is a chance of being detected. Pickpocket Chance = (Thief Sneak Skill * fPickPocketActorSkillMult + fPickPocketActorSkillBase) + (Target Sneak Skill * fPickPocketTargetSkillMult + fPickPocketTargetSkillBase) + (Item Value * fPickPocketAmountMult + fPickPocketAmountBase) 40+(0.6\times\text{Player Sneak})-\left\lceil\frac{\text{Item Value}}{2}\right\rceil-(0.6\times\text{Target NPC Sneak})=\text{Success Chance}

Planting items
The player character can also use pickpocketing offensively to plant a live explosive. This will detonate after a short time, automatically killing the target regardless of the PC's Explosives skill or the target's health or resistances. Non-player characters will notice the pickpocketing of other non-player characters, and begin the [DETECTED] sneak state.

Fallout/2
Reverse-pickpocketing explosives will make an NPC explode according to the timer. This will turn nearby NPCs hostile, even if not having been caught doing anything. If the first explosion did not kill the NPC outright, they will turn hostile. Reverse-pickpocketing is the only way to sneak-attack using explosives, as deploying and dropping armed bombs will cause hostility. If a bomb cannot be planted without being detected, it can be planted on another NPC near the target, or in a container nearby.

Fallout Tactics
Only explosives with a timer such as dynamite or plastique can be planted, but not the remote detonator trap which needs a detonator (once the frequency is set, the trap is automatically laid on the ground). To plant an explosive, a player must take it in a hand, set the timer, then take it back to their inventory and plant it in the NPC's inventory via pickpocketing.

Fallout 3/New Vegas
Pickpocketing and reverse-pickpocketing of NPCs reduces Karma so long as the NPC is not evil. The technique can be used to obtain weapons and armor currently equipped by essential NPCs. Reverse-pickpocketing an explosive in a child's inventory will result in adding it to their inventory with no explosion.

To make an NPC switch armor, an item that occupies the same slot must be reverse-pickpocketed onto the NPC. Upon the next cell reload, which can be triggered by waiting a few in-game hours, exiting and entering an area, or otherwise passing through a load screen, they will equip the replacement item, putting the target item into their inventory. The desired item can then be pickpocketed as normal. Reverse-pickpocketed armor must have a higher DR value than the target item for the NPC to equip it.


 * Notes
 * Initiating dialogue while having planted an explosive on an NPC works even while they are searching for the explosive.
 * When planting armor on a child, even Tesla armor, it adjusts to an appropriate size when equipped.
 * The Paralyzing Palm perk can be used to pickpocket a character without alarming other characters around.
 * Pickpocketing from "good" or "neutral" characters will result in a Karma loss.
 * It is not a hostile act to look in people's pockets or look in an owned container and not take anything.
 * Any item with a value of 190 caps or more will only have a 5% chance of success, even with 100 Sneak or with using a Stealth Boy (formula fPickPocketMaxChance=85 and fPickPocketMinChance=5).
 * Argyle refers to reverse pickpocketing explosives as the "Shady Sands Shuffle."

Fallout 4
Explosives can only be planted on enemies once the Pickpocket perk has reached level 2. It is the only way to give items to dogs who, unlike Dogmeat, do not have a trading system similar to settlers and companions that can be used to equip items.