This chapter explores a clinical case of a patient who presents with worsening abdominal pain. Abdominal pain is one of the most common chief complaints practitioners are faced with across a wide variety of clinical settings and encompasses a broad set of differential diagnoses one must carefully consider. This case in particular emphasizes the importance of performing a thorough assessment and evaluation when red flag symptoms and exam findings are present. This patient scenario further compares and contrasts ulcerative colitis with Crohn’s disease, which are both forms of inflammatory bowel disease that can significantly affect a patient’s quality of life and require a multidisciplinary approach to care. By illustrating key symptomatology, diagnostic features, endoscopic findings, histologic differences, treatment approaches, and potential clinical complications of each of these diseases, students will be well-equipped to properly evaluate and identify similar clinical scenarios in their future practice.