We study in this paper the resolution by single shooting of an optimal control problem with a bang-bang control involving a large number of commutations. We focus on the handling of these commutations regarding the precise computation of the shooting function and its Jacobian. We first observe the impact of a switching detection algorithm on the shooting method results. Then, we study the computation of the Jacobian of the shooting function, by comparing classical finite differences to a formulation using the variational equations. We consider as an application a low thrust orbital transfer with payload maximization. This kind of problem presents a discontinuous optimal control, and involves up to 1800 commutations for the lowest thrust. Copyright c 2000 John Wiley & Sons, Ltd.