Pyoderma gangrenosum (PG) is a rare neutrophilic disorder that typically presents as painful, ulcerative lesions. It is a diagnosis of exclusion and is oftentimes associated with systemic conditions such as inflammatory bowel disease, rheumatoid arthritis, and other inflammatory conditions. PG remains difficult to diagnose, and a delay in recognizing the disease can contribute to appreciable morbidity in the population. Here, we present the case of a 42-year-old male with the classical subtype of PG in the outpatient clinic who failed three courses of antibiotics before responding to corticosteroids.