In this article we explore the dynamic between the pedagogical and the urban, attending to 'agentive urban learning'. By this we mean processes by which young people build agency in the urban context, in using the resources of the city to develop their own agency, and of developing agency to act within the city. By agency, we refer to the capacity to imagine and act to create individual and collective futures. Our interest is how young people develop such agentive urban learning themselves and how it might be enhanced pedagogically at school and university. Three case studies explore different facets--the first how young people themselves develop this agency in situated settings and the tools that they use to reflect upon the future; the second how digital tools might be used to enhance students' understanding of the city as a site of change, in this instance, climate change; and the third how such agency might be developed collectively in partnership with other city dwellers. We conclude that a diversity of students' engagement in urban contexts of learning offers ways from which to further investigate how identity, setting, and stakeholder relationships matter as part of potentially sustainable agentive learning futures.