Patients with corticosteroid-managed chronic obstructive pulmonary disease (COPD) are at increased risk of Achilles tendon rupture. This risk is further augmented in the setting of an acute COPD exacerbation in which antibiotics may be indicated, namely fluoroquinolones. This case concerns a 76-year-old man who experienced simultaneous nontraumatic bilateral Achilles tendon rupture during an acute COPD exacerbation. Treatment was conservative with analgesics, activity modification, and bilateral controlled ankle movement boots. Surgery was not advised because of his multiple medical comorbidities predisposing him to impaired wound healing and potential amputation. Included is a discussion on the pathophysiology, diagnosis, and treatment of Achilles tendon rupture. There is a need for greater awareness of the risk of Achilles tendon rupture from combined use of corticosteroids and fluoroquinolones. After this report, we hope to raise awareness of this complication and prevent patient suffering.