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Message: <blockquote data-quote="strider13x" data-source="post: 6807545" data-attributes="member: 6701931"><p>Overall I would say let the dice decide when you as DM are not sure, apply Advantage or Disadvantage as appropriate. Keep in mind the motivations of the people that are being fooled, does the orc guard from the previous example really have motivation to be suspect of the additional crate? Or is he just making the rounds so he can get back to his card game? The is no one way to rule any situation which is the best (and sometimes worst) part of DMing! Reward players that are inventive, if they come up with something that you as DM have no contingency for then let them have it! Other times they will blunder all fall into exactly what you expected, then you really let them have it!!</p></blockquote><p></p>