We study the propagation of a Newtonian shock in a spherically symmetric, homologously expanding ejecta. We focus on media with a steep power-law density profile of the form ρ ∝ t -3 v -α , with α > 5, where v is the velocity of the expanding medium and t is time. Such profiles are expected in the leading edge of supernovae ejecta and sub-relativistic outflows from binary neutron star mergers. We find that such shocks always accelerate in the lab frame and lose causal contact with the bulk of the driver gas, owing to the steep density profile. However, the prolonged shock evolution exhibits two distinct pathways: In one, the shock strength diminishes with time until the shock eventually dies out. In the other, the shock strength steadily increases, and the solution approaches the self-similar solution that a shock is a static medium. By mapping the parameter space of shock solutions, we find that the evolutionary pathways are dictated by α and by the initial ratio between the shock velocity and the local upstream velocity. We find that for α < ω c (ω c ≈ 8), the shock always decays, and that for α > ω c , the shock may decay or grow stronger depending on the initial value of the velocity ratio. These two branches bifurcate from a self-similar solution derived analytically for a constant velocity ratio. We analyze properties of the solutions that may have an impact on the observational signatures of such systems, and assess the conditions required for decaying shocks to break out from a finite medium.