Copulatory wounding (CW) is widespread in the animal kingdom, but likely underreported because of its cryptic nature. We use four case studies (Drosophila flies, Siphopteron slugs, Cimex bugs, and Callosobruchus beetles) to show that CW entails physiological and life-history costs, but can evolve into a routine mating strategy that, in some species, involves insemination through thewound. Although interspecific variation inCWisdocumented, few data exist on intraspecific and none on individual differences. Although defensive mechanisms evolve in the wound recipient, our review also indicates that mating costs in species with CWare slightly higher than in other species. Whether such costs are dose- or frequency-dependent, and whether defense occurs as resistance or tolerance, decisively affects the evolutionary outcome. In addition to sexual conflict, CW may also become a model system for reproductive isolation. In this context, we put forward a number of predictions, including (1) occasional CW is more costly than routine CW, (2) CW is more costly in between- than within-population matings, and (3) in the presence of CW, selection may favor the transmission of sexually transmitted diseases if they induce resource allocation. Finally, we outline, and briefly discuss, several medical implications of CW in humans.