We analyze the wave equation in families of pp-wave geometries developing strong localized scale-invariant singularities in certain limits. For both cases of well-localized pp-waves and the so-called null-cosmologies, we observe an intriguing discrete dependence of the existence of a singular limit on the normalization of the pp-wave profile. We also find restrictive matching conditions relating the geometries before and after the singularity (if a singular limit for the solutions of the wave equation with initial conditions specified away from the near-singular region is assumed to exist).