In cross-border estate planning, even the most carefully designed structures can unravel when laws, families, and jurisdictions collide. This session examines how ‘anything that can go wrong, will go wrong’ plays out in real private-client practice and how advisers can anticipate, prevent, and manage the fallout. Drawing on real-world case studies, our panel will explore common and unexpected points of failure: mismatched succession regimes, defective trust and foundation governance, tax-residency surprises, forced-heirship conflicts, overlooked digital assets, and the human element—family dynamics, incapacity, and fiduciary missteps. We will discuss practical strategies to build resilience into international plans, respond to emerging risks, and navigate crises when they inevitably arise. Participants will leave with a sharper understanding of how to stress-test estate plans, communicate risk, and craft solutions that withstand the messy realities of global families.