Insertional Achilles tendinopathy is a complex condition with multiple contributing factors, including biomechanical stress, anatomic variations, and systemic comorbidities. Conservative treatment options, such as activity modification, rest, and physiotherapy, remain the first-line approach. However, for patients who fail non-surgical methods, both traditional open and minimally invasive surgical options are available. The choice of surgical intervention is guided by the severity of tendon degeneration and the presence of bony abnormalities, such as Haglund’s deformity. Minimally invasive procedures are associated with faster recovery times and fewer complications. Understanding each patient's anatomic and pathologic variations is critical in determining the appropriate surgical approach.