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Well, I never suceeded from Bernard in stealing even when I boosted my Pick pockets to 275 with master thievery potions, so I'm not sure what im doing wrong. Wearing leather won't lower my chance THAT much, and people are saying they are doing it easy at 170, I don't get it.
Maybe stealing doesn't even go against your Pick pockets skill, maybe its another skill that checks it, who knows.
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