This paper presents findings from analysis of two learning sites, a classroom and a community-based youth organizing group for Latino adolescents where adult "educators" attempted to promote both critical and civic development for the participating learners. By examining the two unique learning spaces with similar youth development goals, this paper highlights how the structural characteristics of learning settings influence engagement and critical civic development processes. Specifically, the paper highlights how these two locations provided different affordances and challenges for promoting engagement that led to critical civic development.