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Message: <blockquote data-quote="JiffyPopTart" data-source="post: 7833320" data-attributes="member: 4881">In my game...IN ROUNDSYou roll the skill check and generally get to keep trying if you fail.  You are using up actions as a cost of failure even if there is no other associated cost.OUT OF ROUNDSIf failing a check has some game affecting penalty (you try to Persuade the guard to give you his key, if you fail you must spend an hour finding a different guard) then you still have to roll to see if the penalty is applied or not.  If the penalty is repeatable you must keep rolling until we establish the cost of getting the skill check accomplished.If there is no penalty for failing a check then you just succeed without rolling and we move on.  UNLESS I have some reason to switch this up, in which case I might tell you to roll and if you fail I will create a penalty to be overcome before you can try again....I would have guessed every game ran this way but maybe not?I switch up some out of rounds checks reinforce the idea that adventuring life is more than what you can do when fighting others.  Making the occasional outside-of-combat-skill-check have higher stakes rewards players who have focused on abilities/spells/items that can be used outside of combat in creative ways.  5e rules as written don't do the best job at engaging the players outside of "encounters" or during downtime.</blockquote>