The rising use of endovascular techniques utilizing femoral artery access may increase the frequency with which surgeons face the challenge of hernia repair in reoperative groins—which may or may not include a vascular graft. We present a case where a vascular graft contributed to an acute presentation and complicated dissection, and review the literature. A 67-year-old man who had undergone prior endovascular aneurysm repair via open bilateral femoral artery access and concomitant prosthetic femorofemoral bypass, presented with an incarcerated, scrotal inguinal hernia. The graft with its associated fibrosis contributed to the incarceration by compressing the inguinal ring. Repair was undertaken via an open, anterior approach with tension-free, Lichtenstein herniorraphy after releasing graft-associated fibrosis. Repair of groin hernias in this complex setting requires careful surgical planning, preparation for potential vascular reconstruction and meticulous technique to avoid bowel injury in the face of a vascular conduit and mesh.