At level 15, put 700 gold in the victim's inventory and steal it back.

If you already have enchanting at 100 and the dual enchanting perk, craft a set (amulet, ring, boots and gloves) with +40% pickpocket and +40% sneak each.

The guards will not take everything out when you get arrested.* 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. Once you have all of his belongings replace them and repeat as much as you want. 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 would like. 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. Once there break free, find your loot and kill all the guards (there are two).

A very easy way to level up the technique is to get sent to Riften jail.

Making mass pickpocket runs through these 3 cities alone while using rested bonus and The Thief Stone will bring a character up to at least 90 Pickpocket in little time. Solitude, Whiterun, and Windhelm have disproportionately higher numbers of people who are more wealthy and carry the above types of items in abundance. Therefore, as a general rule, it is most efficient to pickpocket gold, arrows, gems, jewelry, and other items with little-to-no-weight and high gold value. The chance for success is reduced based on how heavy and valuable the item is. The higher this ratio for an item, the more Pickpocket experience is gained after a successful grab.

The amount of Pickpocket experience gained per item taken is partly based on a ratio of (item value/item weight).

Vipir the Fleet (Master): Thieves Guild in Riften.

Oghma Infinium – choosing the Path of Shadow increases all Thief skills, including Pickpocket, by five.

See each book's page for a list of possible locations.

The following books provide a permanent one-time increase to the Dragonborn's Pickpocket skill. Silently harm enemies by placing poisons in their pocketsĬan pickpocket equipped weapons (when hidden)Ĭan pickpocket equipped items, clothes and armor (when hidden) +25% chance to pickpocket if the target is asleep Item weight and value reduce pickpocketing odds (+20% per additional rank) The following are the perks that become available to select as the skill is leveled up: Governing Guardian Stones: The Thief Stone However, the item's value determines how much the skill is leveled by after being successfully pickpocketed. The amount and weight of an item determines the difficulty of pickpocketing it. 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.

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 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. Gold from training or bribes will also be in the characters' inventory which can then be stolen with the Pickpocket skill. Many characters will carry large amounts of gold or valuable jewelry that is frequently enchanted. There are many opportunities for lucrative pickpocketing to offset the significant costs of investing perks in the skill. A skilled pickpocket is less likely to be caught and is more likely to find valuables.' ― Loading Screens

'The stealthy art of picking an unsuspecting target's pockets.

Lvl 100 pickpocket skyrim