We report the case of an elderly Asian man where a medical error and diagnostic delays obscured the diagnosis of pleural tuberculosis (TB). The patient was hospitalized for evaluation of a unilateral pleural effusion. Initially, the patient was subjected to a pleural aspiration on the wrong side due to a lack of bedside ultrasound guidance. Subsequently, the patient underwent several investigations but not a blind closed pleural biopsy (BCPB) due to a lack of equipment. Furthermore, the patient was deemed to be too sick to undergo a thoracoscopic pleural procedure. Eventually, a bronchoscopy was performed, and washings from the right upper lobe were cultured, which established the diagnosis of TB. This case highlights the need to use bedside ultrasound in the investigation of pleural effusions, the role of BCPB especially in frail patients and finally the utility of bronchoscopy in establishing a diagnosis of pleural TB.