We consider optimal control problems involving two constraint sets: one comprised of linear ordinary differential equations with the initial and terminal states specified and the other defined by the control variables constrained by simple bounds. When the intersection of these two sets is empty, typically because the bounds on the control variables are too tight, the problem becomes infeasible. In this paper, we prove that, under a controllability assumption, the “best approximation” optimal control minimizing the distance (and thus finding the “gap”) between the two sets is of bang–bang type, with the “gap function” playing the role of a switching function. The critically feasible control solution (the case when one has the smallest control bound for which the problem is feasible) is also shown to be of bang–bang type. We present the full analytical solution for the critically feasible problem involving the (simple but rich enough) double integrator. We illustrate the overall results numerically on various challenging example problems.