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.