A 69-year-old man with chronic obstructive pulmonary disease (COPD) presented with an exacerbation of cough and breathlessness, as well as a 5 day history of sudden-onset bilateral calf tenderness. He had been commenced on inhaled steroids 41/2 years earlier and then received maintenance oral prednisone. Upon examination, there was a haematoma inferior to the medial malleolus with no Achilles tenderness on the left side. On the right side, there was focal tenderness over the mid-portion of the Achilles tendon with pain accentuated upon dorsi flexion. A venous duplex study confirmed superficial venous thrombosis involving the left gastrocnemius vein extending proximally to the popliteal vein junction. The major axial deep veins of the left lower leg were patent. Findings on the right side were normal. A subsequent diagnostic ultrasound demonstrated unequivocal bilateral Achilles tendon ruptures. The patient subsequently underwent corrective surgery. There have been several reports of bilateral Achilles tendon rupture associated with long-term corticosteroid use. It is likely that this entity is underdiagnosed because of a lack of awareness of this association by physicians. Recognition and surgical intervention are likely to reduce morbidity and improve outcome.