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Osteoporosis is an important cause of fractures in postmenopausal women. Bisphosphonates are the first line of treatment for osteoporosis. However, long-term use of these medications has been related to atypical femoral fractures (AFF). We present a case of a 71-year-old postmenopausal woman, with a history of osteoporosis being treated with bisphosphonates for 6 years. The patient developed pain in her left hip and thigh over a period of 3-4 months. Radiographic studies showed an AFF and she was managed conservatively. Stopping bisphosphonate therapy should be an initial step in managing or limiting the progression of AFF. A drug holiday should be considered in patients who have been treated for more than 3-5 years to prevent AFFs. The risk of developing AFFs should never be ignored in this subset of patients.