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If a pickpocketed NPC does not find you, they will exit the alert stage and you can safely talk to them without incident. But things have happened to the latter, and its come out the other end darker, matured, and delectably intoxicating. They can wait outside of town or in a far-off location where your victims will not find them. The former is light, fresh, unadulterated. Before pickpocketing, send the rest of your party far away so you do not have to deal with them while sneaking/retreating. Originally posted by Sleazy Ninja: Because otherwise you would be able to pickpocket - sell them the item - pickpocket it again - sell again - ad infinitum. They will only alert others and attack if they see you after they realize they have been robbed - so you can sprint away safely right after a successful pickpocket. Because otherwise you would be able to pickpocket - sell them the item - pickpocket it again - sell again - ad infinitum. Complete a pickpocket, then immediately retreat out of the area so they do not see you. After robbing an NPC, they will realize they have been robbed after a few seconds. You can completely rob traders - so check to see if there is a spot you can enter stealth near shops whenever possible. If you find a target with lots of stuff to loot, dump all your points and enhance Thievery as much as possible to get the most value out of a wealthy NPC. You can only attempt to pickpocket a target once. Reach at least Thievery 4 for the best results. Divinity: Original Sin 2 doesn't include 'classes,' per se. It also helps to collect armor or gear that further enhances Thievery. Note: You can respect at any time to drop all your points into Thievery and Sneaking if you want quick money. Once successfully start pickpocketing you will open a menu showing you the target's inventory and can attempt to take their items. The prerequisite for pickpocketing is to have at least one point in the civil ability thievery. Sneaking reduces vision cones, making it easier to avoid detection, while thievery enhances the amount of gold you can loot, and improves your pickpocketing and lockpicking skills. Pickpocketing works by entering sneak mode and then clicking on an NPC that possesses an inventory for you to pickpocket. Put points into the Thievery and Sneaking skills to earn a lot of gold by pickpocketing in town.