Advantage Doesn’t Stack
Advantage is a simple rule that describes when a player has the upper hand on a roll. Has a fighter positioned themselves perfectly for a swing with their axe? Roll with Advantage! A Wizard has been trying to puzzle out an ancient magical lock, but now they have the instructions? Roll with Advantage!
Advantage can apply to any roll at the table. When the Game Master deems it’s appropriate, they will tell the player to “Roll with Advantage”. The player will attempt the roll as normal, except rolling two d20s (instead of one) and choosing the higher roll before adding their bonuses. Disadvantage works the same way, just in reverse. A player rolls two d20s and chooses the lower roll.
One important rule is that Advantage doesn’t stack. This means there is no such thing as double Advantage. If a fighter gains Advantage from attacking a monster while it’s prone but also had gained Advantage on the same roll because the Cleric used the Help action, it’s still just one Advantage. Even if the player has 20 circumstances that give them Advantage, it’s still just one Advantage.
Similarly, Advantage and Disadvantage cancel each other out. A fighter attacking with Advantage on a swing, standing in terrain that gives him Disadvantage, will roll as normal. Even having multiple Advantages on a roll will be canceled out by a single Disadvantage.