Teachers are expected to be self-directed and to instill in their learners the ability to self-regulate their own learning processes. There are however personal and contextual factors that promote or inhibit teachers' abilities to develop self-regulated learning skills. This study was conducted in two South African secondary township schools and in two Namibian rural secondary schools. Twenty-eight, conveniently and purposively selected teachers participated. This qualitative case study, was intended to provide food for thought about the uniqueness and challenges of township school and rural teachers' perceptions and practices to develop self-regulated learning skills. Data were collected via observations and semi-structured interviews. The results indicate a need for interventions to train practising teachers to be activators and facilitators of SRL skills.