Rupp redshirted the 2008 college track season to focus on the 10,000 m at the 2008 U.S. Olympic Track and Field Trials, where he finished second (27:43.11), earning a spot on the 2008 U.S. Olympic team. He went on to finish 13th in the 10,000 m at the 2008 Olympics with an American Olympic-record time of 27:36.99.