This article focuses on experiences of welfare recipients summoned to do volunteer work. Proponents of ‘workfare volunteerism’ argue that it leads to empowerment and employability while critics dismiss it as disempowering, stigmatising, and disciplining. Our longitudinal qualitative inquiry into experiences of sixty-six ‘workfare volunteers’ in the Netherlands shows how experiences of disempowerment or empowerment are dependent on caseworker approaches as well as on time. Disempowerment can turn into empowerment when an individual's past is considered, but can revert to disempowerment if changing needs go unrecognised. These findings have broader implications for debates on activating policies. They point to the need for diachronic approaches, which reflect the changing experiences of target groups over time and adaption of policies and caseworker approaches that respond to their clients’ changing needs and self-understanding.