Drawing on self-report data from a Learning Criminology Inside initiative bringing together BA Criminology students from the University of Manchester with prison-based students from a category C resettlement prison, this article will consider the process of studying desistance “together” in this collaborative setting. It will discuss the complexities of facilitating an external University course in a category C resettlement prison and illustrate how many of the expected and observed behaviours of both sets of students and staff involved reflected themes common to research in reintegration and desistance. The experience of taking part in a prison-based university level course incurs setbacks, as does desistance, and to overcome these, subjective and structural elements similar to those identified in research around desistance from crime are required. Consequently, while discussing desistance, students (and staff) were also practicing elements of it, especially internal factors such as self-determination and persistence and structural factors in terms of support. This paper will also show the possibilities of learning desistance together for both traditional university-based and prison-based students, including, contact with people who can see the new version of “self”, a support system, and ideas for new pathways to follow.