Syncope is a common chief complaint in the emergency department (ED); however, the workup of syncope is quite extensive. Likewise, community-acquired pneumonia (CAP) can also be difficult to diagnose due to the wide range of signs and symptoms, and even a larger list of etiologies. Syncope as a presenting symptom of CAP has demonstrated to be a challenging clinical association to make. We present a case of a previously healthy 14-year-old female who presented to the ED for having an episode of syncope at softball practice. Notable aspects of the case-age of the patient and the obscure presentation, as well as laboratory and imaging results-made this case challenging. Thus, obtaining a thorough history from the patient and family and performing a detailed physical examination can really help a clinician lead to an accurate diagnosis.