One mini-exploit for levelling Pickpocket is to repeatedly steal the Strange Amulet from Calixto Corrium, during the quest Blood on the Ice, as you can immediaely re-sell the amulet to Calixto for 500 gold - which is also one of several great ways to earn gold in Skyrim.Bearing that in mind, the most efficient items to steal are gems and jewelry, as they're high in value but low in weight - which means a higher chance to steal, as weight determines difficulty.The amount of experience gained from pickpocketing and item is based on that item's value, rather than anything like weight or percentage chance of success.Pickpocket is one of the harder skills to power-level, but it's also one of the fastest to level up in terms of the experience you gain from each attempt.
You can buy lickpicks from Thieves Guild members and fences, or alternatively you can in fact use the Skeleton Key, awarded from a latter quest in the Thieves Guild storyline - which we explain how to start in our Faction quests guide - which is unbreakable, but still awards experience for 'failed' attempts to pick a lock.
Lockpicking and Pickpocket are two skills which often go hand-in-hand - probably because, to gain access to locked doors, there's normally a choice available to the player: lockpick the lock, or pickpocket the key.
Watch on YouTube The fastest way to max level Lockpicking and Pickpocketing
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