Achilles tendon ruptures, if neglected or identified late, lead to impairments in function and gait. Surgical reconstruction is typically required to restore the resting length and tension to the gastrocnemius-soleus complex. A variety of reconstructive options have been described, depending on several factors, including chronicity, residual gap size, remaining tissue quality and vascularity, location of tendon rupture or deficiency, and patient-specific factors. Despite the many surgical options described from local soft-tissue rearrangements and tendon transfers, to the use of allograft tissue and synthetic material augmentation, there is understandably a paucity of evidence-based guidelines available to direct surgeons in the optimal procedure for each patient-specific situation. Reconstructive options for the patient with a chronic Achilles rupture are detailed and reviewed here, to serve as a framework for the treating surgeon in these complex cases.