Primary spontaneous pneumomediastinum is a rare, often benign and self-limited condition defined by air within the mediastinum. However, correctly distinguishing primary spontaneous pneumomediastinum from secondary causes, especially esophageal perforation, remains a diagnostic challenge. There is significant debate regarding the balance of completing a thorough but not overly invasive and costly diagnostic workup. This clinical review aims to gather the limited data regarding spontaneous pneumomediastinum management from case series and retrospective cohort studies, and presents an evaluation algorithm and treatment plan stratified by clinical history. Understanding specifically if the patient presents with coughing versus forceful vomiting is critical to help elucidate the etiology and guide management of pneumomediastinum. Patients who present with forceful vomiting or retching should be considered with higher degree of suspicion for secondary causes of pneumomediastinum, specifically esophageal perforation. However, especially in children, aggressive diagnostic workup is not warranted in every case. After ruling out other etiologies of pneumomediastinum, spontaneous pneumomediastinum can be commonly treated with symptomatic management without the aggressive use of antibiotics or diet restriction. Hospital length of stay may also be minimized on a case-by-case basis. Overall, recurrence of spontaneous pneumomediastinum is rare and outpatient follow up may be safely limited to those at highest risk of recurrence.