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Iv'e been trying to find an all in one pickpocket addon that could help with letting you know if an enemy is pickpocketable or not and if you've already pick pocketed it.
Other than just trying and being told "No Pockets" or "Has already been picked" is a little frustrating.
It could be as simple as adding information into the tooltip, or somewhat advanced by marking targets in some way so you can visually tell.