This paper discusses insights from a larger study of popular educators' deployment of Freire's pedagogical principles during facilitator training. The paper focuses on data from two facilitators and attempts to examine how popular education principles are applied in two different socio-economic and political contexts, Canada and South Africa. Freire's early work on popular education traditions formed the base of the theoretical lens; Foley's theory of ideology with other critical theorist's concepts and critiques of Freire are drawn upon to analyse the evolution of Freire's critical pedagogy and to examine what factors affect its deployment in different contexts. The research design is grounded in interpretivist epistemology and uses a case study approach to examine Freire's pedagogical approaches in two different contexts. Three forms of qualitative data collection tools were utilised: semi-structured interviews, observations and document analysis. Key findings from this study illuminate the influential significance of facilitators' individual ideologies and organisational cultures and demands. It describes how education's relationship with the state must be analysed to assemble a comprehensive understanding of what social and political factors affect pedagogical choices and styles. This study offers more knowledge to the literature concerning the recontextualisation of pedagogy and the factors that affect it.