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Mind that the security skill check is done every time you want to move an item from the "victim" inventory to yours - and maybe the difficulty increases as well, I don't know for sure. Anyway, don't get greedy: if you succeed in opening the inventory without being caught, just go for what you need, don't press your luck unless you want to be caught.
Pickpocketing is a difficult thing to do, even with high skills, so save your game before trying anything
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Never attribute to malice that which can be ascribed to sheer stupidity
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