In Ilott v. The Blue Cross, the UK Supreme Court restated the centrality of the principle of testamentary freedom in English succession law. This chapter considers the principle’s application in the context of will and trust disputes in Hong Kong, an English common law jurisdiction that is not only influenced by Chinese culture and traditions but also serves as a hub for mainland Chinese entrepreneurs who may be subject to the forced heirship laws of civilian China. The chapter has two objectives. First, it reviews recent notable family inheritance cases pertaining to the application of the testamentary freedom principle in Hong Kong to examine how the balance between personal autonomy and familial obligation is struck. Second, as the preference for testamentary freedom also informs the law of private express trusts, the chapter discusses the use of trust and family trust litigation involving some of Hong Kong’s wealthiest families to highlight the most attractive features of the trust device for managing Asian wealth, as well as the corresponding theoretical issues raised by such features.