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Message: <blockquote data-quote="drjones" data-source="post: 6370941" data-attributes="member: 62944">Look at how the 4e save mechanic that was partially imported into 5e dealt with duration.  Rather than roll 1d4+1 for how long the debuff lasts the target gets a save each turn, statistically the result is similar.I can think of fun instances where a skill check can work in a similar way.  The simplest being, party is being threatened on one side of the door and the thief is picking the lock with a hard difficulty.  By allowing rerolls you set a timer on how long it will take to get through.  Yes, getting through is inevitable but it does not feel inevitable because if it takes too many tries there will be an orc spear  up the thieves bum.  And while success on the first round is possible it is unlikely meaning tension can build and players can use creative tactics to assist with the unlocking or dealing with the threat.I guess I don't see how 'No, never' or 'yes, always' are as satisfying in play as 'maybe, sometimes'.  I do thank that new DMs and players should probably lean towards 'yes, always' because they are the ones most likely to not be making perfect decisions both in adventure design and in dungeoneering.</blockquote>