Is there a certain range you have to be away from them when they notice, so that they dont suspect you? Is there a way to avoid this as i, that they don't even notice after you stole the item that its gone? Not as in they caught me, but some time after I successfuly got the item, they'll freak out about something missing. I see that I can sneak up and pickpocket people, get items successfully, but sometimes the person who got pickpockteted will randomly freak out that something was stolen. You can then dismiss them and hire a different mercenary and repeat the same process.Have a rogue with thievery/pickpocket and am trying to figure out what the exact mechanics of it are.
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