Service-learning environments are complex learning contexts that generate a level of disequilibrium or anxiety that may or may not result in transformative learning. This phenomenological study examined student reflective writings from an Honors service-learning course at a medium-sized mid-western university for evidences of transformative learning, the precipitating disequilibria, and the significant pedagogical structures underlying growth. Although all students learned and encountered disquieting experiences, only half the participants exhibited levels of transformative learning. Results indicate that transformative learning requires time, space, and appropriate scaffolding to develop or augment personal internal systems of adjusting what one thinks and how one thinks about new information and experiences. The results further suggest that a framework of iterative service experiences, grounded in course content, readings, faculty-student-community dialogue, and continuous, thoughtfully designed, reflective practice can maximize transformative learning potentials. Future research should continue to explore how service-learning is experienced by individual participants and what contextual factors are essential for increasing the likelihood that transformative learning will occur.