In this study, we closely followed two teacher candidates (Scott and Dan) and their mentors through their student-teaching residencies using the following two questions to guide our investigation: (1) what did teaching look like in Scott's and Dan's classrooms? and (2) how did key student-teaching residency structures and forces enable and constrain Scott's and Dan's teaching practices? Using cultural historical activity theory (CHAT) as a theoretical lens, we found that although both candidates were given marks of proficient to excellent on the formal student-teaching assessments, the social and cultural complexities in their contexts held significant supports for professional growth for one candidate and hinderances for the other. This holds implications for teacher preparation programs with regard to program and candidate evaluation.