J's Pickpocket Skill notes:
QuoteAdded the Pick Pocket player tool, which is available to all PCs who have invested at least 1 point in the Pick Pocket skill.
Rogue level is added to all pick pocket skill checks
You cannot pick pocket:
Yourself
DMs
Anyone that you've attempted to pick the pocket of in the last 30 minutes (unless the last attempt happened during a previous EFU session)
While in combat
NPCs
Targets that you can't see
Anyone further away than RADIUS_SIZE_SMALL
With a DM present today I attempted to do a pickpocket in Town Square.
Hostile, use the Playertool to pick a PC's pocket and the result was 1 coin. So I sought to move on to the next target a few feet over to only find the message "You cannot pick that target's pocket again for x time", despite never hitting this person before with a pickpocket. I attempted it on another PC I had never encountered and it presented the same message as if I had already pickpocketed them even though I hadn't.
It seemed likethe tool itself is on cool down rather than the individual target I hit, unable to pick any more pockets for 30 minutes after tagging one.
I believe it is intentional that you can only pickpocket once in a cycle, with a cooldown.