The last decade has seen a rapid increase in the number of high-profile divorce cases involving wealthy individuals with substantial assets held in offshore trusts. Matrimonial legislation in many common law jurisdictions now expressly empowers family courts to include trust interests in divorce settlements. This chapter examines, from two perspectives, the vulnerability of the trust device when trust law intersects with family courts charged with ensuring the equitable treatment of spouses in post-divorce asset allocation. First, it examines the tension at play when family courts apply matrimonial legislation which may subvert legitimate trust structures designed for careful and tax-efficient management of family wealth. Second, in light of offshore legislation that aims at safeguarding offshore trusts from external interferences, the present chapter addresses the additional interface between the onshore courts and offshore legislation in resolving matrimonial disputes. It concludes by commenting on the prospects of the modern international trust device for confronting these challenges.