By Dr. Sarang Desai — Fellowship-Trained Orthopedic Foot and Ankle SurgeonSports Medicine | McKinney and Flower Mound, Texas The Short Answer If you have deep pain at the very back of your heel — right where the Achilles tendon meets the bone — that hurts most with the first steps in the morning, gets worse going uphill or on stairs, and makes the back of a stiff dress shoe unbearable, you likely have insertional Achilles tendinopathy. Here's the most important thing I tell p