This study provides a detailed account of dilemmas experienced by community organizers arising from the tension between political and educational objectives within the community organizing social action approach. We address the way these dilemmas emerge during nonviolent direct action (NDA), and the associated organizers' valuative processes. Within the course-of-experience framework, we conducted direct field observations, video recordings, and self-confrontation interviews with French organizers promoting housing rights in working-class communities. After outlining six episodes experienced as dilemmatic by these organizers, we offer an in-depth analysis of two enacted prototypical dilemmas. Findings reveal the cruciality of the organizers’ emotions during NDAs, and that organizers tend to prioritize short-term political goals over longer-term goals of collective radical education/emancipation processes. We discuss findings through two main drivers for organizers’ training: the risk of becoming a winner-almighty organizer instead of promoting actual grassroots participation, and the impact of anger and indignation in ethical reasonings during NDAs.