Sweet syndrome (SS) or acute febrile neutrophilic dermatosis is a rare inflammatory skin condition presenting as an abrupt onset of painful erythematous plaques or nodules, fever, and neutrophilia with histopathology showing a dense neutrophilic infiltrate. Systemic corticosteroids are the gold standard treatment for SS. We describe a case of a 26-year-old with a past medical history of ulcerative colitis on chronic prednisone presenting to the hospital with a 3-week ulcerative colitis flare with concomitant erythema nodosum and SS. While SS is well described, this inflammatory skin condition is uncommon in the setting of chronic anti-inflammatory medication.