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The chance of making a successful steal is dependent on your pickpocketing score. It doesn't mean that 100 point in pickpocketing will guarantee success - it won't, because most merchants have very high negative modifiers. 200 points is usually sufficient for most merchants. Place some points into pickpocketing, or use the *stackable* Potions of Master Thievery (which is a top contender for the cheesiest item in the game, IMO).
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