In his retirement announcement, Ragan affirmed he was still open to racing part-time. On January 10, 2020, he announced that he would compete in the Daytona 500 with Rick Ware Racing, who partnered with Front Row Motorsports for this race to field Ragan's entry in the renumbered No. 36 Ford (usually the No. 53). The No. 36 was previously run by FRM teammate Matt Tifft in 2019 until the team scaled back operations. As part of this deal, FRM then leased the charter for the No. 36 (which they had kept for Ragan at the Daytona 500, giving him a guaranteed starting spot in the race) to RWR to use for the No. 53 for the remainder of the season. Ragan would qualify 30th in the 500 and go on to finish fourth, his first top-five since 2015 and his best ever finish in a Daytona 500, despite damage from one of the Big Ones occurring during the race.
