Research on teacher well-being that works from a localized socioeconomic perspective tends to neglect the nestedness of teacher well-being within wider systems. Randomized controlled trials are illustrative of such decontextualized ontological and epistemological foundations. In this article, we demonstrate the benefits of a system dynamics cultural political economy-informed analysis for research on teacher well-being in protracted crises. Zooming into teacher contract and salary policies in the Democratic Republic of Congo, we compare our largely qualitative research with two randomized controlled trials. Our article yields two insights for future systemic analyses of teacher well-being in protracted crises. First, such research necessitates a methodological design that captures the multiscalar systems in which teacher well-being is embedded. Second, such research requires an exploration of cultural, political, and economic dynamics that affect teachers and establish boundaries for teacher well-being.