Abstract: Truck platooning refers to a convoy of digitally connected automated trucks traveling safely with a small inter-vehicle gap. It has been identified as one of the most promising and applicable technologies towards automated and sustainable freight transportation. Although truck platooning delivers significant energy-saving benefits, it cannot be realized without good coordination of drivers’ shifts to lead the platoons subject to their mandatory breaks. Therefore, this study aims to route a fleet of trucks to their destinations using the least amount of fuel by maximizing platoon opportunities under the regulations of drivers’ mandatory breaks. We formulate this platoon coordination problem as a mixed-integer linear programming problem and solve it by CPLEX. Numerical experiments are conducted to demonstrate the effectiveness and efficiency of our proposed model. In addition, we also explore the impacts of drivers’ compulsory breaks on the fuel-savings performance. The results show a slight increase in the total fuel costs in the presence of drivers’ compulsory breaks, thanks to driving-while-resting benefit provided for the trailing trucks. This study may serve as a guide for the operators of automated freight transportation.