From Path of the Vampire Wiki
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Often referred to as 'stealing' (not to be confused with the skill), this article will give a brief overview of what to expect when picking pockets. Although you can gain large amounts of cash from picking pockets, it is not a very efficient way to gain experience.
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To steal from a character or a group of humans, click the "$" sign next to their name on the grid or, when stealing from a group of humans, you may use the keyboard shortcut P. Your success will be determined by your Stealing skill and your Dexterity stat.
When picking pockets, either steal money or items can be acquired from humans. Items can be sold at all shops except for the gift shop. Some of these items are useful for rituals or for crafting special items such as traps or gadgets.
You are more likely to get more money from a larger group of humans than a small one. The reason for this is that, normally, people feel safer in large groups so they are more likely to be relaxed and careless. Also, people sitting alone in parks or deserted areas are very likely to be bums, whereas people in banks are more likely to have money on them.
You can steal from many human NPCs by picking their pockets, as you would with humans or other players. Like PVP stealing, picking an NPC's pocket costs 1 energy.
Be aware, picking the pockets of NPCs only has -- at best -- a 35% chance of success. Activating Phantom Thief 2 gives a 100% success rate against certain NPCs. The success rate is less than 35% if the NPC is especially dexterous or intelligent. Not all NPCs can be stolen from: you cannot steal from animals, undead, cops or hunters.
If you successfully steal from an NPC, you will randomly gain a loot item the NPC usually carries. The chance of getting great loot is exactly the same as it would be if you killed the NPC. If you fail, you can still walk away instead of fighting the NPC if you wish - or turn around and kill it for a second chance at the loot they possess.
- Gangster Example: You managed to slip an item (Crystal Meth) out of the target's pocket without them realising.
If you try to steal from a human in the square before -or- after attempting to steal from an NPC in the same square, even after dispatching that NPC by attempting to kill it (successfully or not), you will receive:
You have already tried stealing from people here today, you should try a different area to be safe.
So be mindful of which NPC you are trying to steal from; regular humans, or specialized ones, since you only get one chance per square.