Realms of Arkania: Blade of Destiny

You can earn this achievement in multiple places, but to make things quick, I recommend heading to the tavern in the starting town, Thorwal. Leave the Temple (?) and head in the opposite direction of the door. Straight ahead, past the merchant stalls, is the tavern. I recommend saving before you try this.

Once inside, press to open the action wheel, and then select "talent". This will open a selection of activities that you can do based on your party. Choose pickpocket, and then choose someone in your part to do the deed.

You need to fail your encounter, so don't pick a party member that has high success. Look for negative numbers. If you do end up being successful, just try it again. If you aren't, then you'll be thrown out of the tavern for being caught stealing. This will pop the achievement.