We're using 5e and OGL. The barbarian in my campaign had a slightly similar request. She's dragged the sword attack down for a 'to hit' roll, but uses the following macro to ask if it's rage, critical or both for determining damage. So she clicks the first button to hit, and if it hits, clicks the button that runs this: ?{Options| Normal, **Normal** Target takes [[1d8 [Sword]+[[@{selected|strength_mod}]] [Str]]] HP. | Rage, **RAGE** Target takes [[1d8 [Sword]+[[2]] [RAGE] +[[@{selected|strength_mod}]] [Str]]] HP. | Critical Hit, **Critical Hit** Target takes [[2d8 [Sword]+[[@{selected|strength_mod}]] [Str]]] HP. | Rage & Critical Hit, **RAGE & Critical Hit** Target takes [[2d8 [Sword]+[[2]] [RAGE]+[[@{selected|strength_mod}]] [Str]]] HP. } So from two choices, you get four outcomes (none, choice A, choice B, choice A&B). You're looking at three choices (rage, divine, GWM) which gets exponential: (none, Choice A, Choice B, Choice C, Choice AB, Choice AC, Choice BC, Choice ABC). Now, my Ranger on the other hand doesn't like one big long list and prefers to be asked the questions sequentially. He still drags his weapon from his character sheet down to his bar for the attack roll, but his damage macro looks like this: /roll { [[1d8]] [Bow damage]+[[@{selected|dexterity_mod}]] [Dex] + [[?{Critical Hit?|No, 0|Yes, 1d8} [Crit!]]] + [[?{Hunters Mark?|No, 0|Yes, 1d6} [Hunters Mark]]] + [[?{Hail of Thorns?|No, 0|Yes, 1d10} [Hail of Thorns]]]} Same end result, but he gets prompted one question at a time and incrementally adds the damage.