This study explores how seven middle and secondary teachers understood and developed ambitious pedagogies within the context of their own classroom. Although there has been an emphasis on preparing preservice teachers for utilizing ambitious pedagogies, these practices are often not observed in practicing teachers' classrooms. The purpose of this study was to gain an in-depth understanding of how teachers understood their own enactment of the pedagogies. Multiple case study methodology was used to explore differences within and between cases. Data sources included teacher self-evaluations, teacher videos of their own practice, and written self-reflections. Analysis of the data revealed three trajectories of teacher development for the enactment of ambitious pedagogies. Four teachers consistently enacted the three ambitious pedagogies in their lessons, one teacher began to enact ambitious instruction practices although inconsistently and two teachers did not successfully enact ambitious pedagogies. Analysis of teacher self-evaluations and reflections revealed teachers that implemented ambitious pedagogies were able to accurately self-evaluate their own teaching practices. This research also found the alignment between a teachers' individual belief systems and ambitious pedagogies was necessary for accurate self-evaluations and reflection. Finally, this research found implementation of ambitious pedagogies was dependent upon a teachers' ability to elicit and respond to student thinking.