Long antegrade cephalomedullary nailing is the standard of surgical care of atypical subtrochanteric fractures of the femur. Long nailing of such fractures is a technically demanding procedure. Our case report discusses the management of sequential bilateral atypical subtrochanteric fractures in an elderly female patient and the technical issues pertaining to nailing of such fractures. During the nailing procedure of the second fracture, an intraoperative distal peri-implant fracture occurred and it was addressed with the application of a distal femoral locking plate. At 2 years postoperative follow-up, the patient was ambulating independently and had sufficient range of motion in both hips and knees.