There's no easy way to roll two numbers, display them separately, and also add them together and compare them to see if they are the same number. (We'll see if RainbowEncoder posts something ingenious that does exactly that, because it involves Reusing Rolls , which I still can't fully wrap my head around.) Here is a macro for Daggerheart rolls , which allows for adding/subtracting 1d6 for advantage/disadvantage, as well as adding a modifier: &{template:default} {{name=Duality}} {{Hope=$[[0.computed]]}} {{Fear=$[[1.computed]]}} {{Total=[[ [[1d12[Hope] ]] + [[1d12[Fear] ?]] ?{Advantage|Regular, |Advantage,+ 1d6|Disadvantage,- 1d6} + ?{Modifier?|0}}}]] }} (Example Roll with Advantage and a +3 modifier) d I'm guessing that once Daggerheart is officially released and a character sheet becomes available on Roll20, it'll have Custom Roll Parsing built in to simplify all of those rolls. As far as changing the colors of the dice, the answer is no, you cannot change the die numbers to display different colors. The colors that are displayed in chat for dice rolls are hard-coded: Red = lowest die roll Green = highest die roll Blue = both lowest and highest die roll Grey = die that is not included in final result (rerolled or dropped)