Its when stay behind a npc longer enough with them noticing you. That is when the success pops up. It also depends on what they are doing. If they are doing something it is easier but if they are just standing there they are more alert.
Ok, that makes sense. I've seen go from 40% to 60% for a hot second right as I get in range, and I've seen it jump from 60% to 85% after I sit there for some time.
There also seems to be diminishing chances the more you pickpocket the same person in a very short period of time. Not sure what the timer is, but I went from a jump to 80% and then a jump to on next try 50% and then only to 40% on the next when stealing from the same NPC.
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