Physicians sometimes are challenged with clinical presentations that do not fit perfectly within the AMA Guides to the Evaluation of Permanent Impairment (AMA Guides); in such cases, the evaluator is instructed to apply clinical judgment and common sense when determining an impairment, with particular consideration of the effect of the medical condition on the individual's activities of daily living. In this case presentation, a 35-year-old male private security guard injured his right elbow performing a bench press while on assignment. After magnetic resonance imaging and electrodiagnostic evaluation, the patient underwent surgery that included a medial elbow Nirschl procedure and an ulnar nerve submuscular transposition. The patient underwent twelve months of rehabilitation, but he continues to experience a pins-and-needles sensation and perceives upper arm strength loss. Twenty-four months after surgery, the patient declines surgical treatment for quadrilateral space syndrome and presents for an impairment rating evaluation. Accepted medical conditions under the workers’ compensation program include quadrilateral space syndrome, medial epicondylopathy, and ulnar nerve entrapment at the elbow (cubital tunnel syndrome). The AMA Guides, Sixth Edition, does not include a listing for quadrilateral space syndrome, and the author discusses the challenges of teasing out functional limitations when multiple diagnoses are present within the same limb. Evaluators should note that the AMA Guides recommends using the impairment rating that most closely represents the actual functional loss.