The Aaron said: GroupInitiative was actually originally designed with just this use case in mind. Unfortunately, it’s a bit harder to use that way after the advent of Character Sheets on Roll20. Before Character Sheets, the only way you could have an attribute was to explicitly create it. Now attributes are implicitly created by Character Sheets. This is important for understanding GroupInitiative’s group system. Each rule group you create will only be applied if all the attributes exist. In the old days, that was obvious and automatic in the use of characters. The implication is that you can make a group that combines character sheet attributes (implicit and explicit) that will always be applied (this is the only rule in the modern usage), then you can create 1 or more rules promoted before it that contain attributes that are manually added which will only be applied if that attribute exists. So, you might make a couple rules like this: !group-init --add-group --bare cunning --bare has_strategist
!group-init --add-group --bare quick
On Characters with strategist, you manually create an attribute named has_strategist with a value of 0. It’s important that the added attribute isn’t one that is implicitly in the character sheet. With these rules then, it will apply the cunning attribute on all the characters with that manual attribute, then skip down and apply the second rule on everything else. Hopefully that will let you get it working right! Again, thank you, i'm gonna check this out!