Ailments of the Achilles tendon are on the increase and present in athletic and sedentary patients. The management of tendinopathy and rupture is not codified; Achilles tendon rupture and tendinopathy can be managed conservatively or surgically. Tackling the complications that arise from the management of these conditions provides a formidable challenge to the surgeon. Rupture, rerupture, disordered scarring with potential keloid formation, nerve damage (especially the sural nerve), poor healing, infection, bleeding and hematoma formation, wound dehiscence, deep vein thrombosis (DVT), and loss of function have been reported. This article gives an up-to-date account on our personal views of managing complications following Achilles tendon rupture, tendinopathy, and delayed rupture.