Bisphosphonates have been accepted as the first-line treatment for postmenopausal osteoporosis. Atypical femoral shaft fracture is one of the side effects of long-term bisphosphonate therapy. The mainstay treatment of this atypical fracture is bisphosphonates cessation and stabilization with internal fixation. We are reporting a rare case of a blocked intramedullary femoral canal found during surgery of an 85-year-old Indian lady with an atypical femoral shaft fracture related to her five-year alendronate therapy. We found difficulty in passing the guidewire through the fracture site during the closed method, which renders open reduction to manage the obliterated intramedullary canal. The importance of changing decisions intraoperatively should be highlighted to avoid further complications. Fracture union is achieved during our follow-up in the clinic.