This research shows that the out-of-field teaching phenomenon tilts teachers’ dispositions toward a pattern of observable challenges for their wellbeing, confidence, feelings of belonging and self-efficacy. This paper unveils how the out-of-field phenomenon influences not only teachers’ wellbeing but also students’ wellbeing and school leaders’ effectiveness. This cross-national phenomenological research involves a developed and a developing country. The results capture lived experiences of leaders, teachers, and stakeholders linked to the out-of-field teaching phenomenon across metropolitan and rural schools at primary and secondary levels. Findings indicate the interwoven complexities of the phenomenon, and leadership's understanding, awareness and engagement improves leadership for wellbeing in the out-of-field context. The paper concludes with an emphasis on the need for noticing teachers’ wellbeing with a context-conscious enactment of micro-education policies to address specific wellbeing needs.