Research has established a relationship between the organisational commitment of teachers and some key teaching-career related variables. However, there has not been any exploration of organisational commitment in Eastern Caribbean schools. Using a cross-sectional research design, we surveyed a sample of 158 teachers to investigate relationships between organisational commitment and selected variables (i.e., career advancement opportunities, principal leadership style, teaching experience, and training). Findings revealed that primary school teachers reported higher levels of organisational commitment than secondary school teachers. However, no significant differences were found in the organisational commitment of trained and untrained teachers, nor were any found between organisational commitment and the other teaching career-related variables included in the study. We discuss the nuanced nature of organisational commitment in schools in Barbados and the Eastern Caribbean that lend to critical policy initiatives.