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Skyrim Skills and Perks Guide: Pickpocket

Pickpocket is the art of picking an unsuspecting target's pockets. A skilled pickpocket is less likely to be caught and is more likely to find valuables.

Spends points in this perk tree if you are playing a thief like class, or if you want to get some extra income

Level up your pickpocket skill by successfully pickpocketing people or by talking to a pickpocket trainer

TRAINERS

Journeyman Trainer: Ahkari (Khajiit Carvans)
Expert Trainer: Silda the Unseen (Windhelm)
Master Trainer: Vipir  (Riften)

PERKS

Light Fingers (1/2/3/4/5)
Pickpocketing bonus of  20/40/60/80/100%. Item weight and value reduce pickpocketing odds.
Requires: Pickpocket 0/20/40/60/80

Note: Core pickpocket perk. Take as soon as possible to increase pickpocketing success chance.

Night Thief
+25% chance to pickpocket if the target is asleep
Requires: Light Fingers, Pickpocket 30

Note: Great for going on a pickpocketing spree at night

Poisoned
Silently harm enemies by placing poisons in their pockets
Requires: Night Thief, Pickpocket 40

Note: Great perk for assassinations

Extra Pockets
Carrying capacity is increased by 100
Requires: Night Thief, Pickpocket 50

Note: Great for carrying a lot more stolen goods!

Cutpurse
Pickpocketing gold is 50% easier
Requires: Night Thief, Pickpocket 40

Note: Take this and get a massive bonus to pickpocket chance when pickpocketing gold

Keymaster
Pickpocketing keys almost always works.
Requires: Cutpurse, Pickpocket 60

Note: With this skill you will almost never fail when pickpocketing keys

Misdirection
Can pickpocket equipped weapons
Requires: Cutpurse, Pickpocket 70

Note: Great way to disarm a target

Perfect Touch
Can pickpocket equipped items
Requires: Misdirection, Pickpocket 100

Note: Great way to strip enemies off armor before going in for the attack!