A 68-year-old female with end-stage heart failure presented to the hospital for heart transplant. She was diagnosed with achalasia 14 months prior and treated with frequent botulinum toxin injections. She underwent orthotopic heart transplant on the day of admission and was extubated a few days later. She developed intractable nausea and vomiting. Her first endomyocardial biopsy revealed moderate, approaching severe rejection. She was treated with high-dose intravenous pulse steroids. Fluoroscopy at the time of follow-up biopsy showed undigested pills in her esophagus with narrowing at the distal end and thus failure to deliver immunosuppressive therapy. This case highlights achalasia as an etiology for acute rejection and its potential management.