Four patients with femoral neck fracture following healed intertrochanteric fracture were evaluated retrospectively. This situation is a rare occurrence with a current literature review documenting only 15 cases. Patient charts and radiographs were retrospectively reviewed to evaluate the period from initial injury to definitive treatment for the femoral neck fracture. Emphasis was placed on associated risk factors and operative techniques. In case 1, the femoral neck fracture appeared to be clearly a traumatic fracture as it occurred 11 years after the intertrochanteric fracture. In cases 2, 3, and 4, multiple factors were believed to play a role in the generation of the femoral neck fractures, which occurred within 6 months of the original fracture. The etiology of such fractures remains speculative. All four patients were elderly, women with substantial medical comorbidities. Osteoporosis may be the most important single contributing factor to these fractures. Because management of this patient subgroup is notably more complex, surgeons need to be aware of the difficulties and prepared to deal with them.