At the 2016 Olympic Games in Rio de Janeiro, Brazil, DiRado won four medals – two gold, one silver, and one bronze. On the first night of competition, DiRado touched second in the 400-meter individual medley in 4:31.15 behind Katinka Hosszú, who broke the world record. She also won a bronze medal in the 200-meter individual medley in a personal best time of 2:08.79, behind Hosszú and Siobhan-Marie O'Connor who won gold and silver respectively. Even though she did not swim the 200-meter freestyle at Trials, DiRado was placed in the finals relay lineup for the 4×200-meter freestyle relay by the coaches. Along with Allison Schmitt, Leah Smith, and Katie Ledecky, DiRado won her first gold medal of the Olympics. In her final event, the 200-meter backstroke, DiRado again faced Hosszú, who was favored to win the event. Hosszú led for the entire race until DiRado surged in the last 25 meters and out touched Hosszú by 6 one-hundredths, 2:05.99 to 2:06.05, for the win.