Managing pneumonia, especially when complicated by underlying anatomical anomalies, presents unique challenges that require a nuanced and multidisciplinary approach. Dysphagia lusoria, a rare vascular anomaly where the right subclavian artery originates aberrantly, can coexist with other thoracic conditions, complicating both diagnosis and treatment. Understanding the interplay between such anomalies and common infections like pneumonia is crucial for optimal patient outcomes. This case report describes a 33-year-old male with a history of recurrent pneumonia in the past who presented to the emergency department (ED) with right flank pain and dyspnea persisting for one week. Initial investigations revealed moderate parapneumonic pleural effusion and right lower lobe pneumonia. At the time, an aberrant origin of the right subclavian artery (ARSA) (dysphagia lusoria) was incidentally detected on imaging. The patient’s management included antibiotic therapy tailored for pneumonia and the placement of a chest tube for pleural effusion drainage. Despite intermittent dysphagia, surgical intervention for dysphagia lusoria was deferred due to its minimal impact on daily functioning. The patient improved significantly with supportive care and antibiotics, highlighting the complexity of managing pneumonia complicated by anatomical anomalies. This case underscores the importance of multidisciplinary management and tailored treatment strategies in addressing intricate clinical scenarios.