Is the 5e Rogue Assassin's Assassinate feature affected by rolling a natural 20? My fellow players and DMs have different opinions.
The Rogue Assassin's Assassinate feature on page 97 of the PHB says:
You have advantage on attacks rolls against any creature that hasn't
taken a turn in the combat yet. In addition, any hit you score
against a creature that is surprised is a critical hit.
During that attack roll on the surprised creature, what if you roll a natural 20, which counts as a critical hit in 5e? Do these two instances of a critical hit stack? If so, would it be double the amount of dice rolled, would it be tripled, or even worse quadrupled?
Maybe you can help end the debate amongst my group.
Best Answer
If you hit, it is already considered a critical hit
This is the case regardless of whether you then roll a natural 20 or not.
When the Rogue is assassinating a surprised target, it will be a critical hit regardless of what the roll of the d20 is, providing of course you still beat the target's AC.
So no, the critical hits do not stack