If you drag an extra copy of your weapon(s) onto your sheet, it should give you another copy in the Attacks & Spellcasting section. Change the name to (for example) Dagger (Crit), and change the Crit Range to 2 (a 1 should still miss). Any roll of 2 or higher will cause the damage link to roll crit damage. If you're playing with API scripts enabled, you could use a ChatSetAttr macro to modify the crit range on the weapon, then change it back after the attack, instead of needing a second copy. You could also use a Query instead, but it'd pop up every time - I'd go with the extra weapon entry, personally, as it won't be interrupting every other round of combat with unnecessary pop-ups. A Query would just need this: ?{Attack type|Normal,20|Assassinate,2} entered into the Crit Range field. Sneak attack damage you can deal with in a bunch of ways, depending on preference. You can use another Query in your normal damage section, add it into the damage 2 section, or even have a link in each of your weapons to a sneak attack macro. For example, change the damage type in the attack settings from Piercing to Piercing - [Sneak?](~SneakAttack) , then create a macro called SneakAttack in your Attributes & Abilities tab which does something like: &{template:simple}{{rname=SNEAK ATTACK}}{{mod=[[ceil(@{level}/2)]]d6}}{{normal=1}}{{r1=[[[[ceil(@{level}/2)]]d6]]}} That'll give you a clickable button in your weapon damage roll that will roll SA damage for you. There's a bunch of macros floating around for dealing with sneak attack in different ways, it's really about personal preference, and how often you're using it. Personally, I don't like rolling any superfluous dice, so I wouldn't have anything set to auto-roll (like the damage 2 field) unless it's applicable to that attack... but that's just me!