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."

- Loading Screens

Pickpocket is a skill in and is one of the six skills that 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 Dragonborn is free to peruse their target's inventory, without breaking the law. Unsuccessfully removing or adding an object will raise the Dragonborn's bounty, often causing the intended victim to become hostile.

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 NPCs 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. This problem can be avoided altogether by paralyzing the victim first, as it is possible to pickpocket anything from them without detection as they are getting back up.
 * Governing Guardian Stones: The Thief Stone

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

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

Trainers

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

Leveling techniques

 * Tested Xbox360 - Easy theft/higher theft chance: Simply put, steal the gold, gems, jewelery and weaponry LAST. Tested with multiple bandits across multiple saves; attempting to steal the gold in victim's inventory first will fail 90% of the time. Stole arrows, foods, various misc. items first, then stole weapons, then gold last. Using this technique managed to completely rob 6 bandits clean of all items in a row without detection.
 * A very easy way to level up the technique is to get sent to Riften jail. Once there break free, find your loot and kill all the guards (there are two). After you have done this sneak up to another prisoner in his cell (One is to the left from your cell, one opposite your cell, Brand-Shei below your cell if A Chance Arrangement is completed, and one opposite Brand-Shei's cell), you can pick pocket all of his belongings. Even if you get caught it will not cause hostility or raise your bounty (because you are already in jail) so just continue to pickpocket him as long as you'd like. Once you have all of his belongings replace them and repeat as much as you want. A far quicker method is planting gold on the prisoner and stealing it back (consult value in bullet below) *Note that you can leave your things in the dresser inside your jail cell. The guards WILL NOT take everything out when you get arrested.*
 * The best way to level it up is to find a carriage driver, like Bjorlam in Whiterun. Save the game first! Open his inventory and go to your 'misc' section. Deposit 200 gold then, without exiting the inventory, steal it back. From skill level 5-20 you should do about 50 gold. From 21-25 you should do about 200 gold. From 26-40 skill do 300 gold. From 41-65 do about 520 gold. From 66-80 do 600 gold. From 81-100 steal around 900 to 1000 gold. Each time you take the money back you will go up by about 1 pickpocket level. This method can also be applied to Sibbi Black Briar. Note: Use as many perks in pickpocket as you can, so you don't get caught as much. This can also be done with guards in a hold. The guard next to Belethor's goods, during the early morning hours is an excellent place to level. Just be sure to keep some extra coin on you to pay your bounty.
 * One method is to get Breezehome, tell Lydia to follow you, give her all your junk, tell her to stop following you, then steal it all back. Repeat ad infinitum making sure to rest in bed every eight hours to get the skill bonus. Note that items will get the "stolen" tag.
 * Steal gold from your Housecarl. Wait until your Housecarl go to sleep, after that place some amount of gold as shown above depending on your level and steal them back. Save the game after two or three tries so you won't miss the opportunity to steal again in case your Housecarl notices you.
 * One method, which avoids potential accidental deaths, is to steal from city guards. This provides the possibility of continually finding someone to pickpocket and being caught instantly upon failure (thus avoiding potential deaths of aggressive characters resulting from a failed pickpocket attempt).
 * A simple and effective method is to quicksave before each attempted pickpocket. If successful, save again, if unsuccessful, re-load. Inns and marketplaces are good places for pickpocketing, as there are many individuals there, who can be pickpocketed one by one, and then move to the next marketplace/Inn. Also, to increase the chance of success, only pickpocket 1 item at a time.
 * Complete the city influence quests and pickpocket anyone with impunity. If caught, just tell the guard that "you're with the thieves guild." This tactic results in a 12 gold fine each time one gets caught.
 * The chance of successfully pickpocketing an item is put into a percentage at the bottom of weight and value.
 * As Guild Master in the Thieves Guild, it's possible to pickpocket any of the members freely. When caught, the member would say, "You could've just asked." Afterwards, it will not be possible to pickpocket that member again, and the message, "__________ has already caught you," will be displayed.
 * Prior to becoming the Guildmaster, Mercer Frey is a good target, since he carries a variety of items, ranging from simple potions to jewels. If he catches you, he will never become hostile or make any commentary. Pickpocket him when he is behind his desk.
 * It is possible to pickpocket a skill trainer, so after being trained in another skill, remember to pickpocket the trainer. In high levels of training, like 70+, with perks in pickpocketing, or a boost with equipment enchantments and/or potions, it's possible to level up quickly by stealing back around 2000+ gold with 90% chance of success.
 * Alternatively, training pickpocket with Vipir is a great way to level the skill early on. Talk to him, train the skill, save, and then try to pickpocket the money he received for the training, reloading upon failures. Each pickpocket attempt will be around a 37% chance, but will level you each time you succeed. So, training and then pickpocketing the single-training money back will result in fast leveling of both yourself, in general, and the pickpocket skill... up to a point. He may, eventually, create so much money on his person (through some means) that will make it impossible to pickpocket, but this is a great way to level the skill and yourself up until that time.
 * Another good technique is to pickpocket from bandits, as they always carry gold. If the attempt should fail, there are no consequences other than the fight with the bandit. Using this method also helps to level up Sneak, particularly if said bandit is killed with a sneak attack. Using Calm on a bandit while pickpocketing works well to this cause.
 * If you have cleared out the valuables of most people in the game and still aren't at 100 pickpocket, The Fishing Job can be used to gain levels while remaining in towns.
 * During Blood on the Ice, after you sell the strange amulet to Calixto Corrium, you can pickpocket it back and sell it to him again. You gain at least one skill level each time you do this, but it is recommended to have at least 40 pickpocket and several light fingers perks for this to work effectively.
 * With 70 speech you can get the investor perk. Go to Angeline's Aromatics in Solitude and invest the 500 gold with Angeline then steal it back. A bug in the game causes the investment option to never go away. You can give money every time which means steeling back larger amounts and leveling faster.
 * You can get a bounty and let you get caught (you need to be in the thieves guild) and bribe the guard with the more expensive option, then steal it back after, this method is very fast but can be a cost at low levels.
 * Try a pickpocket trainer like Silda the Unseen (Windhelm elder lady beggar, hangs out at forge or fires around town). You may gain 1 skill point, then pickpocket the gold back and repeat the process.  Save before each pickpocket attempt.  Once the cost of the training exceeds your ability to recover the gold, switch to the deposit and recover method for a while.

Removing stolen tag

 * Get a Hold Guard to take the Dragonborn's stolen goods, then tell a follower to loot the evidence chest in that city's prison.
 * Sell the item to a Fence and then buy it back at a much higher price. Speech perks and enchanted apparel can be used to reduce the cost of buying back the item. The Dragonborn can use the Fence perk from the Speech skill to use any merchant as a Fence. This will not work for a few items.
 * If Ahkari has been unlocked as a Fence, you can sell her the items, then retrieve them from the invisible chest beneath her via a glitch or using a console command to access it. This way, you actually gain money from removing the tag.
 * Another more expensive method is to put the item into a merchant shop's inventory, then buying it from the merchant. e.g., waiting for the merchant caravans to arrive at Dawnstar, (making sure their inventory will not refresh after speaking with them), then going to the invisible Dawnstar chest, and putting the stolen item inside that chest. Then buying the item from the merchant like any other item. (confirmation required)
 * It's also possible by putting the stolen items in an empty container from which you can search instead of steal, like some wardrobes, endtables and cupboards in houses or shops. Then after storing the stolen items you have to let a follower loot the container and then trade with him/her. It doesn't always work with containers located outside.
 * Another simpler method is to pickpocket the stolen items onto a bandit, then kill the bandit and loot the items. If you fail, you can use an invisibility potion or spell and hide until the bandit is no longer aggravated. You can also kill the bandit and use the technique on a different one if you are detected.

Trivia

 * One way to completely 100% guarantee a successful pickpocket attempt is to paralyze the target first. As soon as the victim begins to get back up, try to pickpocket them and you will be able to take anything. The stealthiest way to do this is by putting weak paralysis poison in their pocket with the Poisoned perk active (carrying a staff of paralysis or knowing the spell will work, but often attract attention and a bounty for assault). Another technique is to carry a weak bow and arrows, lace your shots with paralysis poison, and fire from a hidden position; with a high stealth skill, this can be done without getting a bounty. Especially useful for stealing large sums of gold after paying a trainer. Tested on Xbox, 100% success.
 * A popular exploit to gain pickpocketing skill is to go behind a jarl (because they normally have expensive things) and take something with the value of around 100 gold and place it in their pocket and then simply rinse and repeat.
 * The chance to successfully pickpocket any item (including gold) is capped at 90%.
 * The value and weight of an item determines the difficulty of pickpocketing the item.
 * It is not necessary to be completely 'hidden' to successfully pickpocket, though it does raise the chance to steal items significantly. It is, however, necessary when pickpocketing equipped items or weapons (though only from the character you're trying to pickpocket - it doesn't matter whether or not others see you, so long as they don't catch you).
 * After unsuccessfully attempting to pickpocket an NPC, the NPC cannot be pickpocketed again for 2 days. The NPC will not reset if the player waits two days in the same room.
 * A Forsworn Briarheart will die if the Briar Heart is successfully taken from his inventory thus making this action double as a "stealth attack" to the Briarheart.
 * It is possible to pickpocket items with a 0% chance to steal. However, it requires having the Poisoned Perk. Simply get any type of paralysis poison and place it in the target's inventory. While they are down, pickpocket the desired item.
 * The above method will also work using a Staff of Paralysis, but will only work on some NPCs while others become hostile. This depends on the NPC's level.
 * Another method to do it is to use Ice Form on the NPC, sneak and pickpocket them just as the ice breaks, friendly NPC like Trainers or Housecarl will not become hostile when you use Ice Form on them. With this method, you can pickpocket both equipped armor marked with 0% chance, as well as gold paid for training.
 * Very weak NPCs may die for frost damage during the freeze time.
 * The Perfect Touch perk does not work on essential NPCs.
 * Relieving hostile NPCs of all weapons in their inventory (including equipped ones which requires the Misdirection perk) will cause them to pick up and equip nearby weapons on the ground or anything with a damage rating and to replace their lost weapon.
 * Every NPC has its own detection status, meaning that as long as that specific NPC can't see you, you still count as 'hidden' to him, even if the eye is completely open.
 * A 0% chance to pickpocket does not mean that it is impossible to steal that item. It means that the chance falls below 1%.
 * NPCs only wear their original apparel. For example, if you pickpocketed Iron Armor off of someone, they will only reequip that and nothing else.
 * You can read a Book or Note while pickpocketing someone, you don't get penalized nor does it increase the pickpocket skill.

Bugs

 * Enchantments that boost pickpocketing chances may reduce the success rate when the base chance is small. (Such enchantments grow less effective as the value of the item being pickpocketed increases; for the most difficult items, these bonuses fall below 0%, resulting in a negative "bonus").
 * In a similar circumstance such as above, the disease Ataxia ("Reduced Lockpick & Pickpocket";"Picking locks and picking pockets is 25% harder.") serves to benefit the player by instead increasing the chance to pickpocket very high values. For example; targeting Eorlund Gray-Mane, item "Gold (2173)" with a 85% chance with the disease present, item "Gold (2173) with a 64% chance after the disease has been cured.
 * If the target is standing up from paralysis, one can pickpocket everything from them without being noticed. However, this will not increase the player's pickpocket level.
 * When quickloading immediately after being caught pickpocketing when subtitles are enabled, the residents will appear to be slandering you as a thief, this however does not make the residents aggressive nor will get you a bounty. To fix this, just exit the city and re-enter.