After-school programs serve as a way to enhance student learning with more flexibility regarding the curriculum and classroom structure. In this article, we reflect on our work with youth from diverse racial, ethnic, linguistic, and socio-economic backgrounds in an after-school program. Applying Youth Participatory Action Research as our guiding framework for teaching and research, we examine the collaboration between middle school and university graduate students in an after-school program. We revisit our written reflections of our collaboration with youth, and identify five prominent themes: (1) student development of critical literacy skills; (2) the importance of using multimodal tools; (3) co-construction of knowledge; (4) youth development of agency, confidence, and mental health; and (5) the messiness involved in the Youth Participatory Action Research process.