In this article, social work theory on reflective practice is used to explore the potential value of reflection on action for professional learning by activation workers who support people receiving welfare benefits to find work. The article focuses on the role of reflection on action in professional learning concerning three challenges which activation workers face: dealing with normative dilemmas, translating formal and informal knowledge into decision-making and dealing with power relations. The article presents tentative findings stemming from qualitative research on Dutch activation workers participating in reflection on action. Participants report multiple learning outcomes concerning these challenges. The theoretical and empirical exploration suggests that reflection on action can support learning by activation workers to better deal with professional challenges inherent to their work. However, these empirical findings are preliminary and based on a specific context. Further exploration by both scholars and practitioners is therefore suggested, in which the social work profession has a lot to offer.