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The current study focuses on the well-being of Montfortian teachers in terms of work engagement in five Asian countries such as India, Singapore, Malaysia, Thailand, and the Philippines. Data were collected using a survey questionnaire from 427 teachers. Differences in the level of work engagement were tested using Analysis of Variance. Regression models examined the significant predictors and organizational outcomes of work engagement. Perceived Organizational Support and Servant Leadership significantly predicted Work Engagement in Singapore and Thailand. Work Engagement had a positive impact on Organizational Citizenship Behavior (OCB) directed toward organizations in Singapore, Malaysia, Thailand, and the Philippines. It had a significant effect on OCB directed toward teachers in Malaysia and Thailand. Work Engagement also predicted Affective commitment in India and Singapore. This study produces cross-national knowledge about work engagement. Further, it provides a better understanding of teachers’ well-being in terms of work engagement and its effect on organizational variables in the school context.