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While Achilles tendon injuries are common amongst the general population, there are very few cases in which simultaneous bilateral injuries occur. Medial malleolar fractures at the time of Achilles tendon rupture have been cited in the literature and are commonly missed. The following case outlines the presentation, treatment, and outcome of a United States Army Soldier with simultaneous bilateral Achilles tendon ruptures in addition to a unilateral right medial malleolar fracture. This patient was able to completely return to duty within 1 year after being treated with ORIF of the medial malleolus, bilateral end-to-end repair of the AT, and accelerated rehabilitation beginning at 2 weeks on the left and 6 weeks on the right.