This chapter explores three context and education system factors that are implicated in educators’ experiences of stress in the workplace: occupational support, interpersonal relationships, and educational policy changes. More precisely, the first factor concerns occupational support provided to educators to conduct their work with a specific focus on principals’ provision of autonomy support. Autonomy support stems from self-determination theory and refers to the extent to which an authority figure supports individuals’ self-determination in a particular context. The second factor concerns the relational context of teaching with a focus on educators’ relationships with students and colleagues. The third factor concerns the impact of systemic factors in educational policy. For this, we have focused on the impacts of standardized testing and educational innovations. Together, the three overarching factors represent defining features of school and educational systems that shape educators’ work and their experiences of stress in that environment. Overall, our aim is to broaden understanding of the role that schools and educational systems play in educators’ psychological functioning at work.