We reviewed a 43-year-old female patient reporting spontaneous onset of sharp pain around the left midfoot with subsequent difficulty in extending the great toe for the past 12 months. She had a history of chronic pain in the midfoot due to osteoarthritis with osteophyte at the talonavicular joint for which she had received multiple steroid injections. Her examination revealed tenderness and a palpable osteophyte at the talonavicular joint. In addition, active extension of the big toe was weak compared to the opposite foot. She was, however, able to bear weight and walk with some discomfort. An MR scan () confirmed the EHL tendon rupture with a retracted proximal end lying at the level of the tibiotalar joint. To address this issue, she was taken up for open surgical repair using a longitudinal incision over the dorsum of the foot exposing the EHL tendon. The tendon edges had retracted with a 5 cm gap between them (). The proximal stump was identified at the level of the ankle joint and the distal stump at the talonavicular joint. The tendon edges were debrided and repaired using a turndown flap technique. The proximal stump was divided along its thickness to lift a flap measuring around 5 cm (). The turndown flap was used to bridge the gap between tendon edges and sutured to the distal stump (). Kirschner wire (K-wire) was used to stabilize the first metatarsophalangeal joint in extension (), and a below knee plaster cast was applied. K-wires were removed at 6 weeks. However, a slipper cast was maintained for immobilization for 9 weeks, after which weight bearing was commenced in a walking boot. She began a range of motion exercises under the supervision of a physiotherapist from 12th week onward. In her latest clinic review, the patient’s pain had entirely resolved, she could actively dorsiflex the great toe, and her Foot and Ankle Ability Measure score had significantly improved from 18/84 pre-operatively to 64/84.