Bisphosphonates have recently been used as a first-line treatment for osteoporosis. However, prolonged bisphosphonate use may be associated with insufficiency and atypical femoral fractures. In this case report, we present a patient with simultaneous bilateral insufficiency femoral fractures after using alendronate for 11 years, which were treated surgically. Our patient also had a history of a previous right femoral atypical fracture eight years before the latest ones, while on 3-year alendronate treatment. To our knowledge, it is the first patient reported with three atypical - insufficiency fractures covering all the anatomical areas of the proximal half of the femur after long-term bisphosphonate treatment.