As the fields of digital humanities and digital history have grown in scale and visibility since the 1990s, legal history has largely remained on the margins of those fields. The move to make material available online in the first decade of the web featured only a small number of legal history projects: Famous Trials; Anglo-American Legal Tradition; The Proceedings of the Old Bailey Online, 1674–1913. Early efforts to construct hypertext narratives and scholarship also included some works of legal history: “Hearsay of the Sun: Photography, Identity and the Law of Evidence in Nineteenth-Century Courts,” in Hypertext Scholarship in American Studies; Who Killed William Robinson? and Gilded Age Plains City: The Great Sheedy Murder Trial and the Booster Ethos of Lincoln, Nebraska. In the second decade of the web, the focus shifted from distributing material to exploring it using digital tools. The presence of digital history grew at the meetings of organizations of historians ranging from the American Historical Association to the Urban History Association, but not at the American Society for Legal History conferences, the annual meetings of the Law and Society Association, or the British Legal History Conference. Only a few Anglo-American legal historians took up computational tools for sorting and visualizing sources such as data mining, text mining, and topic modeling; network analysis; and mapping. Paul Craven and Douglas Hay's Master and Servant project text mined a comprehensive database of 2,000 statutes and 1,200,000 words to explore similarities and influence among statutes. Data Mining with Criminal Intent mined and visualized the words in trial records using structured data from The Proceedings of the Old Bailey Online, 1674–1913. Locating London's Past, a project that mapped resources relating to the early modern and eighteenth century city, and also made use of the Old Bailey records. Digital Harlem mapped crime in the context of everyday life in the 1920s. Only in the past few years has more digital legal history using computational tools begun to appear, and like many of the projects discussed in this special issue, most remain at a preliminary stage. This article seeks to bring into focus the constraints, possibilities, and choices that shape digital legal history, in order to create a context for the work in this special issue, and to promote discussion of what it means to do legal history in the digital age.