January 2017, Earnhardt announced that he would drive the No. 33 Chevrolet for Circle Sport – The Motorsports Group. The following month, Earnhardt made his CS–TMG debut at the Daytona 500, and in his debut with the team, Earnhardt made NASCAR history by becoming the first-ever fourth-generation driver to compete in the Daytona 500. He started 33rd and finished 26th (which tied his career-best finish up to that point) after being involved in a crash on lap 143. Earnhardt raced the full season except for the road courses. Starter sponsored the early part of the season, while Hulu stepped in to sponsor the majority. On October 15, 2017, Earnhardt signed a contract extension to remain with CS–TMG for the 2018 season. However, on December 12, Circle Sport Racing and The Motorsports Group ended their partnership, leaving Earnhardt temporarily without a ride. Earnhardt ended up joining the No. 00 StarCom Racing team for the 2018 Daytona 500, marking the 40th consecutive year that a member of the Earnhardt family had driven in the event. Earnhardt also ran the next four races for StarCom and planned to run the full season for the team, but after the fifth race of the season, he and the team parted ways. On May 22, it was announced that Earnhardt would drive the No. 55 for Premium Motorsports in Charlotte's Coca-Cola 600. The week following the race, he announced more races with the team but did not name an exact number. On July 7, Earnhardt finished 11th at the Coke Zero Sugar 400, which was his career best Cup Series finish up to that point. On July 28, 2018, it was announced that Earnhardt would join Gaunt Brothers Racing in their No. 96 Toyota for 14 races, with sponsorship from Xtreme Concepts. In November 2018, Earnhardt joined Joe Gibbs Racing's for the 2019 NASCAR Xfinity Series season, driving the No. 18 Toyota Supra in nine races and sharing the ride with Riley Herbst, Kyle Busch, and Denny Hamlin. At the summer Charlotte race, Earnhardt scored a career-best third place finish, despite sustaining damage from hitting the turn 3 wall on lap 142. On February 14, 2019, security company and sponsor Xtreme Concepts announced the formation of XCI Racing, which would field the No. 81 Toyota Camry and Supra for Earnhardt at the two Talladega Cup and five Xfinity races, respectively. Although Earnhardt stated that he would