This paper untangles the complex realities of Sexual Reproductive Health and Rights education in Uganda based on a Participatory Action Research with staff and volunteers of an NGO. A detailed portrait is offered of the dilemmas faced by the team around value-contradictions in this culturally sensitive domain, the complex nature of change, programme targets and community expectations. Through double loop learning methodology, the Team reflected on their own mental models and strategies used in dealing with these dilemmas and reframed their action theories towards more effective collaboration with learners and community members. The research process and outcomes illustrate the transformative power of reflection and double loop learning; resulting in practical guidance for education NGOs facing dilemmas in community collaboration.