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There is a guy in the area that seems to have 1500 gold every time I check his inventory. I have a 0% success rate to steal it.

I've taken it every time, and it zooms out like I've been caught, but nothing happens. If I try to steal again in the same area I get 'You've already been caught pick-pocketing'.

So far I haven't found any downside.

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Never thought to try it in there. Do you have a bounty in Riften at all because of it? – Doozer Blake Nov 27 '11 at 18:47
No bounty. I also found 1500 gold on the archery trainer in Ragged Flagon - Cistern, which I stole with the same result. – JoeB Nov 27 '11 at 19:49
Might have found a nice little source of income then, but it sounds like you can only do it once if it gives you the already been caught message. – Doozer Blake Nov 27 '11 at 19:50
It's repeatable. Not sure how long you have to wait. – JoeB Nov 27 '11 at 20:50
You don't get the item (gold) when caught stealing. Lol – user15793 Dec 3 '11 at 15:09

The only penalty is not being able to try again for a while, which isn't really a penalty.

This is the same in Jorrvaskr if you're in the Companions (and I'm assuming the Dark Brotherhood and etc will all be the same).

If you assault them however, you'll have to earn their trust back by paying 1000 gold (which is stupid because I killed the archery trainer after paying him 20,000 gold and only had to give 1000 back).

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Remind me not to offer to train you in anything in exchange for money. – Doozer Blake Nov 27 '11 at 19:54
Cool, I'm leaving open for a little while to make sure there isn't a hidden reason not to do this. – JoeB Nov 27 '11 at 20:50

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