We live in a world permeated with technology. Through our online accounts we write emails, we store pictures, videos, and documents, we pay bills and conduct financial transactions, we buy digital books and music, and we manage loyalty programs. Digital assets have quickly replaced physical letters, pictures, books, compact discs, and documents stored in filing cabinets and shoeboxes. The emergence of digital assets raises pressing questions regarding the treatment of digital assets at an account holder’s death. Unlike digital assets’ physical counterparts, an account holder does not control the ultimate fate of digital assets. Instead, digital assets are controlled by a private contract entered into by an account holder and a company that provides services or digital products. This Article explores the growing conflict between traditional succession practices and digital asset succession, which is controlled by digital asset contracts. It begins by tracing the development of private contracts as a method of transferring assets at death and shows that although contracts are regularly used to transfer assets at death, digital asset contracts have taken an unprecedented step of prohibiting or severely limiting the transfer of assets at death. This Article next explores the prevalence of digital assets and explains how service providers address digital asset inheritance in private contracts. It argues that digital asset contracts that deny inheritance may be validly formed but should be void as a matter of public policy because they transfer decision-making power about assets from an individual account holder to corporations. As our control over the ultimate fate of our digital assets diminishes, the nature of our property interests in digital assets also shifts away from our traditional understanding of ownership of personal property. It argues that we should take a conscious approach to reforming succession law based on time-honored principles of American succession law that benefit society as a whole and not allow private contracts controlling digital assets to hijack our system of inheritance. This Article concludes by offering suggestions for reform and action before the ability to transfer and preserve digital assets falls beyond our reach.