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This study examines how teachers' pedagogical decision making regarding difficult histories is influenced by socio-ecological factors within their professional environments. Using Bronfenbrenner's ecological systems theory alongside concepts of teacher vulnerability and risk-taking, we analyzed interview data from seven social studies (SS) teachers who participated in a university-based professional learning program focused on teaching difficult histories. Findings reveal that teachers navigate complex webs of ecological supports and constraints that significantly impact their willingness to engage students with challenging historical content. Teachers' awareness of their vulnerability and their risk-taking behaviors influence the kinds of classroom spaces they create. This research highlights the need for institutional supports that help teachers develop professional agency while navigating the inherent risks of teaching difficult histories.