Developing a critical-reflective teacher-understanding of teaching practices is an essential element of teacher development on the in-service Diploma of Education programme for secondary-school teachers at the University of the West Indies in Trinidad and Tobago. Teacher development involves engagement with key educational concepts and reflection on practice as teachers facilitate the learning of their charges. Given the post-colonial context characterising the educational system in the West Indies, this research arose out of the need by Social Sciences teacher-educators to find out whether their teachers had developed the kind of critical-reflective understandings that would enhance their classroom practice in an emancipatory fashion. This chapter examines teachers’ understandings of their teaching practices to determine whether these understandings can be classified as emancipatory, given the existing post-colonial nature of the educational system. The study assists the Social Sciences teacher-educators to improve their approach to teacher professional development, a key aspect of which involves the process of teacher reflection whereby teachers interrogate theory, practice and context and integrate improved understandings into their profession in an emancipatory manner. In this qualitative case study, data on teacher-understandings were gathered from teacher-participants’ written teaching-philosophy statements over the duration of the ten-month programme. Data reduction employed thematic analysis. Choice extracts were then presented and discussed in narrative form including observations and implications. Findings indicate that teacher-participants understand themselves as emancipatory agents, take responsibility for individual growth, however their sense of self as part of a professional community needs to be strengthened. They also possess understandings of their subject-discipline and teaching practice that can be considered as emancipatory.