This chapter addresses the challenges and strategies for teaching medical students in Hong Kong to conduct culturally sensitive and effective end-of-life (EOL) communication. Highlighting the coexistence of Western medical frameworks and Chinese cultural values, it examines the limitations of existing models such as SPIKES and the Calgary-Cambridge guide when applied to Hong Kong’s unique healthcare context. Key topics include the influence of family involvement, the cultural taboo surrounding death, and the role of translanguaging in clinical communication. Drawing on case studies and local research, the chapter advocates for a hybrid communication framework that integrates Western techniques with Chinese cultural practices. Practical teaching approaches, including role-playing, simulated patient encounters, and multidisciplinary collaboration, are discussed to prepare students for the complexities of EOL communication. The chapter underscores the importance of culturally informed training to ensure patient-centred, empathetic, and contextually appropriate care in Hong Kong’s multicultural healthcare system.