The U.S. K-12 public education system is fundamentally unequal. What efforts can facilitate students to become deeply immersed in the realities of the system and to embody the need for social change? This article investigates scaffolded, semester-long writing assignments to demonstrate patterns in the three tenets of critical community-engaged learning (authentic relationship development, reducing power differentials, social change orientation). The assignments come from three cohorts of a Sociology of Education course in which undergraduates spent early mornings walking with elementary school children. As efforts were made to deepen the community-engaged partnership, there is corresponding evidence in (1) the ways students humanized social problems through authentic relationship development, (2) the ways they detailed moments of youth-led activities in which power differentials were diminished, and (3) how students' reflective thoughts more frequently focused upon social change.