The lowest level is made of simple opportunists. There are all sorts of pickpockets in the world, working at various skill levels. Silda can be found walking around in Windhelm. The NPC who can train you in pickpocketing is Silda the Unseen. Who can teach me pickpocketing in Skyrim? Don’t try to pickpocket anyone you failed at pickpocketing within the last two days.
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