Semiconcave functions are a well-known class of nonsmooth functions that possess deep connections with optimization theory and nonlinear pde's. Their singular sets exhibit interesting structures that we will describe in thistalk. First, by an energy method, we will analyze the curves along which the singularities of semiconcave solutions to Hamilton-Jacobi equations propagate, the so-called generalized characteristics. Then, we will derive the dynamics of propagation for general semiconcave functions. Finally, we will discuss applications to Monge-Ampère equations and/or weak KAM theory.