The 5th Edition Player's Handbook, Chapter 7, Advantage and Disadvantage (p. 173) says: When you have advantage or disadvantage and something in the game, such as the halfling’s Lucky trait, lets you reroll the d20, you can reroll only one of the dice. You choose which one. For example, if a halfling has advantage on an ability check and rolls a 1 and a 13, the halfling could use the Lucky trait to reroll the 1. When using the Halfling Luck checkbox in the The Roll20 5th Edition OGL Sheet, as described here , it will reroll all ones, as seen in the screenshots below: