Pleural collections on the side of an obstructing bronchial cancer pose a particular challenge. All efforts should be placed into determining whether the collection is malignant or para-malignant with its significant implications on cancer staging. This article discusses various diagnostic modalities and therapeutic interventions needed for the optimal management of patients presenting with this situation. The order of interventions is dictated by the individual circumstances that patients present with, often requiring the pleural interventions to take place ahead of the bronchial obstruction management.