This chapter explores the complexities of teaching clinical communication to medical students in Hong Kong, where the interplay of Western medical frameworks and Chinese cultural values creates unique challenges. It examines the limitations of widely adopted communication models like SPIKES (Setting, Perception, Invitation, Knowledge, Empathy, Summarize or Strategy) and the Calgary-Cambridge guide in addressing the cultural and linguistic nuances of Hong Kong’s healthcare environment. Drawing on a case study of scenario-based role-play exercises for delivering bad news, the chapter highlights the struggles of medical students in adapting Western protocols to local contexts. Key challenges include language barriers, translanguaging practices, and balancing cultural expectations with ethical transparency. The chapter proposes a hybrid framework that integrates culturally responsive communication strategies, emphasizing the importance of medical Cantonese proficiency, family-inclusive decision-making, and reflective role-play learning. These recommendations aim to better prepare medical students for patient-centred care in Hong Kong’s multicultural and bilingual healthcare setting.