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Message: <blockquote data-quote="clearstream" data-source="post: 8505092" data-attributes="member: 71699">Take a look at the rule on multiple checks in the DMG. For there to be a check, we have really three conditions (from RAW). <ol> <li data-xf-list-type="ol">Player does something in fiction (determines what they think, act or say) that in our sole discretion ("ask yourself") engages a game mechanic</li> <li data-xf-list-type="ol">There is something at stake: meaningful consequences </li> <li data-xf-list-type="ol">It must be possible to succeed and fail</li> </ol>Per the multiple checks rule, if it is possible and there are no consequences for failing, they succeed in ten times the time (remember that you are free to vary that.)That means your second intuition is the rightone. There is a way other than roll to resolve uncertainty in cases with no meaningful stakes: time. But say a player insists on rolling to do it faster? They've asked to put time at stake, but here they have erred or are meta-gaming. They tell you what they think, do or say, and you say how that is resolved. If time doesn't really matter, just say yes.I can't tell from this example if there are really no stakes. What happens if the guards see them? Why is that detail important enough to call out?</blockquote>