As a part of a larger-scale research, the present study aimed to use the main tenets of sociocultural perspective; namely, mediation, internalization, zone of proximal development, and the activity theory, to analyze the novice and expert teachers’ professional development through personal practical theorizing as an awareness raising technique. Furthermore, the study attempted to identify the contextual factors hindering teachers’ pedagogical beliefs enactment. The areas of mismatches between the teachers’ beliefs and practices were identified in the previous phases of the study, and personal practical theorizing procedure was implemented in the program to help teachers converge their beliefs and practices. Within the domain of the qualitative research, a multi-case study design was utilized, employing eight novice and experienced teachers who were selected through purposive sampling. The teachers’ professional development in the proposed program was analyzed through the lens of sociocultural perspectives, and the contextual factors hindering teachers’ beliefs enactment were enumerated based on the results gleaned through interview sessions.