The debate on whether interaction with professionals during imprisonment supports desistance or if incarceration itself hinders the reintegration of young adults is ongoing. Research literature tends to emphasize the importance of professional interpersonal skills and attributes in establishing and sustaining good working relationships through genuine care and demonstration of trust, interest and belief. These factors are fundamentally important for professionals to succeed in playing a part in the life of young adults often labelled as “hard-to reach”, as confirmed in this study, which sheds light on what eight formerly incarcerated young men in Norway consider important for prison officers to be seen as a relevant source of support. Despite the widespread experience that incarceration primarily teaches the importance of “masking their vulnerability”, the presence of officers in small everyday interactions where the young men felt understood and accepted as fellow human beings, through small talk and activities, is highlighted in their stories. I argue that these “moments of normality” have the potential to play a role in the identity and relational dimensions of desistance processes, especially for those with limited access to adult role models during and after imprisonment. This raises questions about what it means to be a professional prison officer and whether there is room for these small yet important everyday interactions in hierarchical organizations under economic and evidence-based pressures.