Setting: Physiatry outpatient office. Patient: A 35-year-old woman with bilateral ankle pain. Case Description: The patient, with no significant medical history, presented to the office with a complaint of acute bilateral posterior ankle pain and swelling, 1 week after a 10-day course of ciprofloxacin for a urinary tract infection. Magnetic resonance imaging (MRI) of both ankles showed bilateral partial achilles’ tendon rupture. Assessment/Results: Absent trauma and any significant medical history, the tendon rupture was attributed to the use of ciprofloxacin. Discussion: Fluoroquinolones are extensively used in physiatry practice, especially in an inpatient setting. A few cases have been reported of Achilles’ and other tendon inflammation or ruptures that required surgical repair or resulted in prolonged disability with use of fluoroquinolones. None were noted in the rehabilitation literature. Pathologic mechanism for tendon rupture is poorly understood and may be due to alteration in tendon fibroblast metabolism. Treatment with fluoroquinolones should be stopped at the first sign of pain or inflammation so to reduce the risk of subsequent rupture. This effect is not dose dependent. There is a variable period (3–5d) between introduction of an antimicrobial agent and onset of pain. Pain is the most frequently reported symptom. MRI helps to differentiate between tendinitis and rupture. Conclusion: Fluoroquinolones are widely used in medicine. This case report should make rehabilitation pracititioners aware of this uncommon complication with use of fluoroquinolones.