If you want the player to be able to roll themselves, but you want to put the DC in yourself, you'll need to output a button for them to click on. There's no way to pop up a query in another player's browser without them clicking on something. To keep it simple, I would just call the roll from the sheet and compare to the DC by eye. Here's an example DM macro where you click on the player token to send them a roll button with the skill and DC baked in. /w @{target|t1|character_name} &{template:npcaction} {{rname=Skill check vs DC?{DC?|15|16|17|18|19|20}}} {{name=@{target|t1|character_name}}} {{description=Please roll ?{Which skill?|Acrobatics,acrobatics|Animal Handling|animal_handling} [Roll](`/w gm @{@{target|t1|character_name}|?{Which skill?}_roll}" style="color:blue)}} If you really want the success comparison, that is doable, it's just a lot of work since you'll need to recreate all the goodness the sheet already does for you (global modifiers, advantage & disadvantage, a roll template to make it look pretty) and escape it all inside a roll button. All possible, just more work. If all you want is a button they click on and input the DC themselves, and the success comparison is more important to you: [[{[[1d20 + @{selected|acrobatics_bonus}]],0}>?{DC?|15|16|17|18|19|20} ]] success ($[[0]] vs ?{DC?})