Garnets and other gems are also good targets. Then make a save and attempt to steal that item. To level Pickpocketing faster, find someone with an item that either has very high value or low chance of stealing it.
Silently harm enemies by placing poisons in their pockets. Plus 25% chance to pickpocket if the target is asleep.
Item weight and value reduce pickpocketing odds. These are the Perks available in the Pickpocket perks tree.
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