In recent years, management of osteochondral lesions of the talus (OLT) has improved due to advancements in imaging modalities and surgical techniques. The choice of treatment is based both on characteristics of the patient and the lesion itself. For regular sized and primary OLTs, debridement and bone marrow stimulation remain the surgical treatment of choice. For larger and/or non-primary OLTs, there is a variety of treatment options, all with their own indications, advantages and disadvantages. In general, three main categories of surgical techniques can be identified: (1) repair, (2) regenerate or (3) replace the OLT. Moreover, orthopaedics is alignment and biomechanics, and not just biology. Therefore, a stand-alone or additional calcaneus osteotomy can be a very powerful tool to decompress the affected ankle compartment. This chapter provides an overview of advanced treatment options for larger and/or non-primary OLTs.