How can veterans be supported in their transition into education? Veterans who left military service frequently face severe struggles when they transition into education, which impacts their participation in class, interactions with teachers and peers, and results in alienation and drop-out. International studies relate these struggles to a conflict between habituated military practices and civilian norms. While the transformation of military practices is a central theme in veteran research, current research mostly examines the acculturation of veterans to civilian norms. Going beyond these approaches, our project emphasizes that veterans have an agency in transition, which leads us to explore the non-affirmative aspects of veterans’ transformation. We employ transformative learning theory to illustrate the processes and outcomes of veterans’ transitions into education. Our analysis attends to the transformation of veteran orientations, defined as implicit meaning structures that guide habituated practice and shape how veterans experience and participate in education. Based on focus groups and narrative interviews with veterans about their experiences in upper secondary and higher education, our aim is to present support strategies that veteran support professionals and student support units can use to help veterans in their transition into education.