Boerhaave syndrome (BS) is a full thickness oesophageal tear. Most cases require surgical correction. In rare cases, conservative management can be attempted. This case describes a 30-year-old patient with a history of BS 9 months prior, managed conservatively at that time, presenting with 2 days of vomiting. Their vitals and physical examination were within normal limits. Imaging revealed extensive air tracking along the mediastinum, oesophagus, and bilateral neck and chest wall consistent with BS. Gastrographin and barium oesophagrams showed no contrast extravasation. The patient was successfully treated with conservative measures including pantoprazole, piperacillin-tazobactam, cessation of oral intake, and parenteral nutrition. This case represents one of only two documented cases of recurrent BS in an adult patient in which both cases were managed conservatively. Of these two cases, this is the first report with the second episode of BS occurring more than 4 weeks after the first episode. Additionally, unlike the other recurrent BS case that was conservatively managed, this patient lacked any known comorbid risk factors for development of BS. While the management of this case resembles the care provided in some prior case reports, the significant variation and lack of standardisation in the approach of conservative BS treatment posed a significant challenge in developing a therapeutic plan. Given the absence of high-quality studies about conservatively managed BS, an increased sample size of case reports detailing their non-procedural management approaches and their subsequent outcomes would hopefully eventually clarify an optimal treatment regimen, and allow for standardisation of conservative BS treatment.