TBH no matter how good a dog is I would barely trust it with its own litter, this seems like playing with knives except your hands are kittens.

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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.

Okay but unless his character canonically noticed then this is metagaming.

I feel like those are not mutually exclusive features.