Though teacher educators nationwide are considering ways to provide urban placements for pre-service teachers (PSTs), little research has examined how PSTs experience placements in schools operated by charter management organizations (CMOs). This study considers CMOs—which often hold particular instructional and classroom management philosophies—as a specific type of school-based learning environment. We draw from a Discourse analytic theoretical framework using qualitative methodology to study how three English education focal PSTs experience disconnections between student-teaching placements at CMO schools and their teacher education program. Findings suggest three ways teacher educators can support PSTs in navigating school-based learning. PSTs in this study experienced contexts and philosophies that varied greatly between their schools and teacher education program. Implications include: (1) PSTs must feel that others in their schools value their learning; (2) PSTs in cohorts must feel they belong to learning communities; and (3) PSTs need support in confronting paradoxes they face between theory and practice.