INTRODUCTION Costal margin rupture (CMR) injuries in association with intercostal hernia (IH) are rare and symptomatic and provide a significant surgical challenge. Surgical failure rates up to 60% are reported, and optimal techniques are unclear. We have characterized these injuries and describe the evolution of our surgical management techniques. METHODS Patients characterized by the Sheffield Classification where CMR and IH were both present, either CMR-IH or transdiaphragmatic intercostal hernia (TDIH), were identified prospectively, and injury characteristics, patient management, and follow-up data were recorded. Surgical techniques evolved according to patient outcomes from suture repair without and then with extrathoracic mesh, to three iterations of double-layer mesh repair (DLMR). The third iteration involved DLMR with biologic mesh, titanium buttress plates applied to the ribs adjacent to the IH with intercostal nerve-sparing suture placement. Associated surgical stabilization of rib fractures, or surgical stabilization of nonunited rib fractures, was performed when required, with costal margin plate fixation where possible. RESULTS Of 25 patients with CMR-IH and 11 with TDIH, 25 patients underwent surgery, with 6 reoperations in 5 patients. There were 8 suture repairs and 3 extrathoracic mesh repairs: DLMR was performed in 14 patients (3 Mark [Mk] 1, 5 Mk 2, and 6 Mk 3) with 2, 1, and 0 reoperations, respectively. Costal margin stabilization with titanium plates was successful twice at the level of the seventh but failed twice out of three times at the ninth costal cartilage. Reoperation after a failed mesh repair is particularly challenging and may require the placement of titanium buttress plates, surgical stabilization of rib fractures, and the use of stainless steel wire sutures. CONCLUSION Repair of CMR-IH/TDIH is challenging, but experience-based evolution of techniques has led to a durable and reproducible Mk 3 repair. LEVEL OF EVIDENCE Observational; Level III.