This paper re-considers a recent analysis on the so-called Couplet–Heyman problem of least-thickness circular masonry arch structural form optimization and provides complementary and novel information and perspectives, specifically in terms of the optimization problem, and its implications in the general understanding of the Mechanics (statics) of masonry arches. First, typical underlying solutions are independently re-derived, by a static upper/lower horizontal thrust and a kinematic work balance, stationary approaches, based on a complete analytical treatment; then, illustrated and commented. Subsequently, a separate numerical validation treatment is developed, by the deployment of an original recursive solution strategy, the adoption of a discontinuous deformation analysis simulation tool and the operation of a new self-implemented Complementarity Problem/Mathematical Programming formulation, with a full matching of the achieved results, on all the arch characteristics in the critical condition of minimum thickness.