Heel pain is commonly encountered in orthopaedic practice. Establishing an accurate diagnosis is critical, but it can be challenging due to the complex regional anatomy. Subacute and chronic plantar and medial heel pain are most frequently the result of repetitive microtrauma or compression of neurologic structures, such as plantar fasciitis, heel pad atrophy, Baxter nerve entrapment, calcaneal stress fracture, and tarsal tunnel syndrome. Most causes of inferior heel pain can be successfully managed nonsurgically. Surgical intervention is reserved for patients who do not respond to nonsurgical measures. Although corticosteroid injections have a role in the management of select diagnoses, they should be used with caution.