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I found that the "Dealer" in the Shadow Thieves' Guild could be pickpocketed three times of money (45 to 47 gps) or gems before he was labeled "Target has no items". I found that hilarious

I emptied Ribald Barterman as well, but could not pickpocket anybody else as "important" successfully. I have Yoshimo at level 16, with 110 slots in pickpocketing and wearing the Gloves of Pickpocketing.

Any suggestions?

Hmmm, i'd say give ribald at the adventures mart a try, you can pick up a very nice ring of regeneration. Oh ya, if memory serves me right there is a whole list of nice pick pockets in the stragy guide on this site. I'd probably have to say the best one is picking up the extra ring of gax. Anyway give the guide a look, quite the useful thing.

yeah and it was a waste put 110 in the pickpocket ability, when you want to pickpocket anything its best to drink 5 potion of master thievery and you can pickpocket anything

I like to pickpocket lavok to get a second ring of acuity.

pick pocket the wizard that sends you on the quest after valygar, you can get the ring of ramm off of him.

Most Amnish soldiers carry scrolls for some reason.

Pickpocketing, IMO, is pretty broken as a skill--or perhaps it would be more accurate to say it was never thought out. I would have liked to see more serious repercussions for success and failure: if you succeed, the chance of success lessens, and if you fail, you don't lose access to a merchant, but you do pay an enormous fee (who wants to lose a merchant? Everybody just reloads). I'd like to see high levels of pickpocketing give you an understanding of what a mark is carrying, and an extraordinarily high level should allow you to target a given item.

Originally posted by fable:
<STRONG>I'd like to see high levels of pickpocketing give you an understanding of what a mark is carrying, and an extraordinarily high level should allow you to target a given item.</STRONG>

Yes,that would be very nice,I think they should make pickpocketing similar to stealing from a NPC in Fallout2,where you could see what he had in the inventory,and choose which item you'd like to steal.I also think it should be more difficult to steal larger/heavier (i.e. 2H swords,Plate Mails)then smaller items like scrolls and potions,it just makes more sense to me.

don't forget to pickpocket the genie outsied of the tent in Trademeet. You will be pleasantly surprised.
I also somebody saying that you can pickpocket eihter Renal Bloodscalp or Aran Linvail for a ring of Genie summoning. (never tried it though)

Aran Linvail, well you'll not pickpocket him but you find the ring after killing him when working for Bodhi.
Another tip: some guy on the lower floor of Galwarey Estate should have Mordekainen Sword spell scroll.

To rich peple on deck out side cages random good items