This chapter reports on a qualitative case study that investigated (i) how CPD for teachers contributes to teacher well-being in Botswana and Namibia, (ii) implications the current model of CPD holds for effective teacher learning that promotes positive student learning outcomes, and (iii) implications for policy and practice in CPD for teachers. Data are sourced through document studies, while Bernstein’s theory of pedagogic discourse is used to make sense of the data. The findings reveal a paradox in the preferred model of teacher CPD where, on the one hand, CPD is touted as a tool for promoting teacher well-being, while on the other hand, it contributes to the degeneration of teacher well-being. The findings further reveal that the regulative discourse underpinning the licensing model is likely to lead not only to the degeneration of teacher well-being, but it is also likely to constrain effective teacher learning for promoting positive student learning outcomes. Packaged and transmitted to teachers through professional standards and thriving on reward and punishment approaches, the regulative discourse generates feelings of fear and anxiety among teachers concerning the future of their jobs in the teaching profession. The model aggravates an already appalling situation of challenges and hardships faced by teachers, contributing to the declining teacher well-being and professional self-identity. The study recommends a shift toward a model that supports teacher well-being, development, and professional identity.