As advances in legal technology reshape boundaries between lawyers and clients, some scholars foresee increased access to civil justice. Do-It-Yourself (DIY) estate planning through the use of online forms is frequently offered as evidence of this phenomenon. In this article, I take seriously this prediction, assessing the extent to which technology is likely to increase access to estate planning. In doing so, I identify several themes that complicate predictions for legal technology’s potential to increase access to justice. First, I highlight the potential of legal technology to reproduce, rather than ameliorate, existing social inequalities. Second, I note the challenges raised by complete automation. Finally, I discuss the role of regulatory and doctrinal reforms in determining the trajectory of legal technology. The analysis serves as a useful illustration of the need to ground our expectations for legal technology in empirical realities.