incident with DiBenedetto was one of his "biggest setbacks ever," but acknowledged "hitting rock bottom (after that) was the best thing that happened to me because that really gave me the wake-up call of 'hey, this is only going to get worse, and you're never going to come back from it unless you do something about it right now.'" In 2018, Ware transitioned to motorcycle racing, but returned to the Cup Series for RWR at Dover. He also ran the Sonoma race, where he would DNF and place last. Ware increased his Cup schedule in 2019 to 13 races, which also included the Daytona 500; in the race, he and RWR teammate B. J. McLeod crashed while several cars were entering pit road, causing him to finish 39th. At Sonoma, he was forced to exit the race on lap 64 when broken air conditioning caused him to suffer carbon monoxide poisoning. In September, he intended to race at the Charlotte Roval, but was replaced by J. J. Yeley as he continued to feel unwell from his damaged coolbox in the previous day's Xfinity race. His lone 2020 Cup start was the YellaWood 500 at Talladega Superspeedway. Towards the end of the race, due to a lot of front runners being involved in crashes, Ware was racing in the top ten until he crashed on the backstretch on the final lap, but was able to finish 19th for his first Cup Series top 20. On January 18, 2021, RWR announced Ware would run the full 2021 Cup season in the team's No. 51 car. During the April Martinsville race, Ware was involved in an incident with teammate James Davison: on lap 37, contact from Ware's right front fender into Davison's left rear quarter panel sent the latter spinning into the outside wall. The race was postponed to the next day after weather, and radio communications between Ware and his crew chief revealed displeasure towards Davison, with Ware threatening to turn him if he encountered him again. After the team threatened to park Ware, the two raced for the rest of the event. Ware missed the Richmond playoff race and was substituted by Garrett Smithley after he was sidelined with carbon monoxide poisoning following the 2021 Cook Out Southern 500 at Darlington. At Bristol Motor Speedway Ware got into Chase Elliott, the two would become heated after the race. Ware returned to