This case presents a study of elementary pre-service teachers in the School of Education at Louisiana State University where the majority of the elementary education candidates are White, female, and from middle-income households, but are preparing to teach in public school districts that enroll students who are overwhelmingly poor and Black. This dynamic gives rise to tensions between each group’s lived experiences and requires pre-service teachers to think critically about how their backgrounds and their identities might impact teaching practices and the decisions they make in the classroom. The purpose of this study was to investigate how 26 pre-service teachers’ engagement through academic service-learning promoted critical thinking. Acts of reflection, which are integral to all aspects of teacher education, academic service-learning, and critical thinking served as a means of understanding pre-service teachers shifting dispositions and evaluating teaching expertise. Using two methods of digital reflections—Facebook and a web platform—the primary data sources allowed for immediate and authentic contributions from the participants. Findings yielded from these data sources indicated that embedded service-learning components in professional practice literacy courses promoted critical thinking about teaching and learning, especially when tensions surrounding difference in life experiences surfaced. Three themes emerged from data analysis: overcoming bias, negative expectations, and stereotypes; synthesizing the elements of the instructional process; and achieving reflective praxis.