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If I go to pickpocket a person who's recently caught me, I get an error saying I can't do it because they've already caught me.

How long does this last? Is it indefinite, or will they "forget" after a certain amount of time?

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try this answer: gaming.stackexchange.com/questions/40275/… –  gladius2metal Dec 29 '11 at 6:30
    
@gladius2metal That's good information to have, but I'm still interested in what sort of time limit (if any) is involved also. This is useful for times when waiting could be quicker than dealing with the loading screens between areas. –  Iszi Dec 29 '11 at 6:35

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The pickpocket flag will never reset afaik. When I was testing the answer to the other question, waiting multiple days in the area did not work. I didn't test the super long wait periods (2+weeks) to see if they would eventually reset. And frankly, if anyone's loading times take longer than waiting for 2+ weeks, they probably have bigger issues on hand.

I think you have to force the area to unload and reload before the flag is reset for you to be able to pick pocket again.

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4  
Fast-traveling out of and back into the area did the job. You can't just go in/out of a building - you have to actually leave the zone. (Going in & out of my house in Riften didn't work, but fast-traveling to/from the nearby Stables did.) –  Iszi Jan 30 '12 at 17:45

If you leave the hold and come back (with at least 24 hours in between) the person will be reset.

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Try waiting 24 hours. It worked for me with Eourlund Gray-Mane.

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NPC cannot be pickpocketed again for 2 days. The NPC will not reset if the player waits two days in the same room. –  ヴァイシャリ Nov 7 '12 at 8:18

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