Okay but unless his character canonically noticed then this is metagaming.
this post was submitted on 17 Sep 2024
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"tried" I'm guessing they noticed :p
I think the dnd rules are a little vague on this, perhaps intentionally. It does clearly state you fail a pickpocket if the target passes a perception check, but that doesnt mean every undetected attempt passes nor that you cannot steal when someone notices.
Had a player once try to pickpocket another, it didn't go well.
They passed the perception check, and also rolled a successful hit. Dude dropped like a sack of potatoes.
Don't roll that dice unless you can pay that price
Don't roll that die unless ready to die?