Introduction: This series reviews three cases of back pain where a highly morbid diagnosis was missed by an emergency physician and subsequently successfully litigated. Case Report: We review the clinical entities of spinal epidural abscess and cauda equina syndrome, challenging diagnoses that can be easily missed and lead to patient harm if not treated promptly. Here we offer suggestions for recognizing these conditions quickly, performing an adequate history and exam, and using documentation to support decision-making. Conclusion: When confronted with an unfortunate medical outcome, maintaining honesty is of paramount importance in medical-legal environments.