This chapter aims to encourage historians and criminologists to synthesise historical and contemporary datasets to examine juvenile justice and punishment across both time and space. It outlines the contours of life-course criminological approaches and reviews how historians have utilised the digital environment to examine criminal lives on a transnational scale. Life-course criminologies explore the lives of 'individuals as they move through time and place, and how criminal offending changes and continues with the movements'. It follows that life-course criminologists adopt a longitudinal approach involving the creation of individual biographies of offenders as a way of exploring the relationships between patterns of offending and life-course events. The chapter describes some of the ways that the historical contextualisation of life-course criminology and, perhaps especially, the digitisation of historical data, can signal new directions and open up a range of possibilities for researching the origins and outcomes of juvenile justice in Europe.