Traumatic insemination is a bizarre form of mating practiced by some invertebrates in which males use hypodermic genitalia to penetrate their partner's body wall during copulation, frequently bypassing the female genital tract and ejaculating into their blood system. The requirements for traumatic insemination to evolve are stringent, yet surprisingly it has arisen multiple times within invertebrates. In terrestrial arthropods traumatic insemination is most prevalent in the true bug infraorder Cimicomorpha, where it has evolved independently at least three times. Traumatic insemination is thought to occur in the Strepsiptera and has recently been recorded in fruit fly and spider lineages. We review the putative selective pressures that may have led to the evolution of traumatic insemination across these lineages, as well as the pressures that continue to drive divergence in male and female reproductive morphology and behavior. Traumatic insemination mechanisms and attributes are compared across independent lineages.