At the end of 2001, Pressley was released from Jasper, and he tackled on a new venture, the Craftsman Truck Series. He signed with Bobby Hamilton Racing and won his Truck Series debut at Daytona International Speedway. He also ran the season opening Daytona 500 in Cup for what was the last race for Melling Racing, finishing 22nd. In 2003, Pressley moved to HT Motorsports in the Trucks, finishing 12th in points. He returned to the Busch Series to drive the 47 again for ST Motorsports, finishing in the top-ten twice, before moving back to the trucks with HT in 2005, finishing 20th in the standings.