This paper reports a set of findings from a larger research study undertaken on Physical Education (PE) teachers' career-long professional learning in Greece. In total, nine case study PE teachers participated in the study. Data were collected using semi-structured interviews with the teachers. The data were analysed using a constructivist approach to grounded theory. Most of the teachers had engaged in collegial learning (with "trusted" colleagues) and identified it as supportive, particularly early in their careers. Nevertheless, structural constraints limited the ways in which collegial learning could be progressed, resulting in teachers who--in some cases--developed resilient yet isolated learner identities. However, most teachers in this study thought positively about the possibility of engaging in more structured collaborative learning opportunities. Decoding and explaining the contextual reality of Greek schools is a vital step in the process of introducing new forms of continuing professional development (CPD).