2006–2008
During the 2006 season, Jarrett had four top-ten finishes, with a best finish of fourth at Kansas. His best starting position was second and he finished 23rd in points. It was his last year racing for Yates, as he and his sponsor UPS left for Michael Waltrip Racing's new No. 44 Toyota team.
Jarrett started the 2007 Nextel Cup season on a high note as he drew pole position for the annual exhibition race, the Budweiser Shootout, at Daytona. He finished 18th out of 21 cars. Since Jarrett's team was a brand new team and had no owner points, and due to a rule change, he was eligible to use the Past Champion's Provisional five times as his 1999 championship was the most recent among past champions who were driving for teams not in the top 35 in owner points; prior to the rule change the use of a Past Champion's Provisional was not limited.
Jarrett was forced to use all six of his provisionals at the start of the season, starting at Daytona mainly because Michael Waltrip Racing was penalized by NASCAR for an illegal fuel additive during Speedweeks and the penalties knocked Jarrett, Waltrip, and Reutimann out of the top-35 in owner points-the safety net for qualifying regardless of rain and cancellations of qualifying.
Jarrett started 43rd in the Daytona 500 and finished 22nd. Jarrett used his last champion's provisional at the spring Talladega race, Aaron's 499. For the rest of 2007, Jarrett had to get into that weekend's race on time. Jarrett missed twelve races in 2007 as a result.
During an interview on Speed, Jarrett said after his contract is up with MWR (which was expected to be in the 2009 season), he would retire, but the timetable was pushed up in October 2007 prior to the 2007 Bank of America 500. Jarrett retired from points racing after the 2008 Food City 500, turning the No. 44 Toyota ride to David Reutimann. His final race was the All-Star race on May 17, 2008, after which he joined ESPN's NASCAR coverage full-time as a booth announcer.
However, Jarrett was not guaranteed to start the first five races using the champion's provisional as he had the year before as Kurt Busch, the 2004 champion, had his team's owner points transferred to his teammate Sam Hornish Jr. and would be first to receive it. Jarrett started off 2008 with a sixteenth place finish at Daytona. He retired from points racing after the Food City 500 at Bristol Motor Speedway. At the weekend's pre-race driver's meeting, he spoke to the other drivers, saying
Enjoy this. We all have our time in this, and mine has been fantastic. To me, it has been an honor and a privilege to be able to race in this series and say I raced with and against and sometimes beat the best in the world. Thanks for allowing me to do that. Enjoy it. It's a great sport, and you guys make it what it is.