Osteoporosis remains a chronic and common disease associated with high medical costs. Pharmacological therapy has shown to be a good strategy to significantly reduce fracture risk. While literary evidence for bone protection in the short and medium term is strongly in it's favor, there are concerns about long-term treatment with antiresorptive drugs. Increased risk of atypical femoral fractures (AFFs) have been demonstrated in several studies following the long-term use of bisphosphonate. Denosumab offers an alternative approach to the treatment of osteoporosis, however, it is also an antiresorptive drug. We present a case of simultaneous bilateral atypical femoral fractures in a patient with denosumab treatment. These findings highlight the need to reevaluate the optimal antiresorptive therapy duration, as well as the safety of transition from bisphosphonates to denosumab and the need for continued monitoring in the prevention of AFFs.