[RPG] Natural 20 when rolling with disadvantage

advantage-and-disadvantageattack-rolldicednd-5e

If you are rolling with disadvantage and roll a natural 20 on one of those rolls, which die roll do you take?

My question stems from the fact that natural 20s count as critical regardless of modifiers, but disadvantage means you take the lower of the two rolls.

Best Answer

The rule on modifiers applies only after you've determined a base roll. And to do that you must first resolve disadvantage (PHB page 173):

Use the higher of the two rolls if you have advantage, and use the lower roll if you have disadvantage.

Therefore, you always take the lower roll.

This is a direct inverse of this answer here for rolling a critical miss with Advantage.