Plantar pain is a common complaint among patients who undergo imaging of the foot and ankle. The etiologies of plantar pain are varied and may arise from traumatic, infectious, oncologic, vascular, and systemic inflammatory causes. An understanding of the anatomy of the foot and ankle, paired with knowledge of the patient's clinical presentation and the common imaging diagnoses, allows the radiologist to come to either a definitive diagnosis or a reasonable differential diagnosis that can lead the clinician to the correct diagnosis. Radiography, CT, and ultrasound can assist in diagnosing the cause of the plantar pain. However, MRI plays a dominant role, given its excellent soft tissue contrast and superior evaluation of the bone marrow and soft tissues obtained from a single imaging modality.