AbstractWave propagation in the form of fronts or kinks, a common occurrence in a wide range of physical phenomena, is studied in the context of models defined by their Hamiltonian structure. Motivated, for dispersive wave evolution equations such as a strongly nonlinear model of two‐layer internal waves in the Boussinesq limit, by the symmetric properties of a class of front‐propagating solutions, known as conjugate states or solibores, a generalized formulation based purely on the dispersionless reduction of a system is introduced, and a class of undercompressive shock solutions, here referred to as “Hamiltonian shocks,” is defined. This analysis determines whether a Hamiltonian shock, representing locally a kink for the parent dispersive equations, will interact with a sufficiently smooth background wave without inducing loss of regularity, which would take the form of a classical dispersive shock for the parent equations. This property is also related to an infinitude of conservation laws, drawing a parallel to the case of completely integrable systems.