Purpose: Spontaneous pneumomediastinum (SP) refers to the presence of free air in the mediastinum without an identifiable precipitating cause. While relatively rare and typically benign, SP often prompts thorough investigation due to the need to rule out spontaneous oesophageal perforation (Boerhaave’s syndrome), a condition with high morbidity and mortality if undiagnosed. This study aims to assess the current practices in the investigation and management of SP at our institution. Methods: We reviewed all patients with imaging-confirmed pneumomediastinum at a tertiary hospital between 2014 and 2022. Patients with a history of trauma, recent surgery, or aerodigestive instrumentation were excluded. Results 70 patients were included, of whom 4 were diagnosed with Boerhaave’s syndrome based on CT evidence of oesophageal injury and underwent immediate surgery. The remaining 66 were diagnosed with SP. Common risk factors included younger age, smoking, illicit drug use, and alcohol consumption. The primary symptoms were dyspnoea, chest pain, vomiting, and cough. Of the 13 admitting specialties, respiratory medicine and upper gastrointestinal surgery were the most frequent. In the SP cohort, 54% underwent imaging to exclude oesophageal injury, with 43% using CT with oral contrast, 23% undergoing fluoroscopic oesophagram, and 13% patients evaluated with both. Conclusions: At our institution, SP is managed by multiple specialties, with varying approaches to the use of imaging modalities. We propose a management algorithm to guide clinicians unfamiliar with SP, support accurate risk stratification for oesophageal injury, and minimise unnecessary investigations.