The long-term care of collected and created data is an ethical obligation in the fields of archaeology and cultural heritage management. With the growing application of digital methodologies in these fields and the complexity of the resulting data, this task has become complicated. Digital data preservation firms have emerged since this methodological shift, but their policies—championing the democratization of academic data—may conflict with the legal obligations dictated by the countries where data originate. Scholars thus face an inevitable choice between two obligations, one ethical and one legal. While the amount of digital data grows and the options for preservation remain fundamentally misaligned with research norms and project workflows, the digital dilemma places the integrity of data at risk of loss. This article addresses this dilemma by evaluating the existing data publication, archiving, and preservation repositories and considering how, as solutions to the digital dilemma, they can be integrated into multiple workflows. I also propose new directions for archaeological associations, suggesting that they should establish a means of evaluation and approval for third-party preservation firms managing the future of academic research prior to their inevitable ubiquity.