As the practice of law increasingly deploys digital technology to deliver services and information, more law schools are including instruction in technical skills. The prospect of more lawyers with digital expertise renders salient a potentially overlooked imperative: that instruction in technical skills must be paired with the development of a critical orientation toward those skills that interrogates how the techno-solutionist values exist in tension with legal values of human agency and dignity. This chapter examines the cautions of skills-forward approaches to incorporating technology into law pedagogy and practice, arguing that developing a sensitivity toward the social, economic, and political contexts in which technology is produced is essential to ensuring such expertise is applied in ways that continuously improve the quality of encounters with the law, rather than simply reproduce them in digital terms. Coupling technical instruction with critical approaches to technology can prepare professionals not only to design novel digital solutions in law practice but also to fundamentally improve legal institutions and programs through the design of technology.