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This study examines and conceptualizes the relationship between entrepreneurial teacher leaders and the renewal of pastoral care practices while accounting for any possible mediating effects of new technologies. We collected 446 survey responses from teacher leaders and used structural equation modeling to test the hypotheses. Results suggest that teacher leaders with higher levels of teacher entrepreneurial behavior (TEB) are more likely to renew pastoral care practices, which is mediated by technological opportunism. The results contribute to the literature on teacher leadership and pastoral care strategies, highlighting the importance of TEB in sustainable development. Furthermore, the study demonstrates that teacher leaders with strong TEB are more receptive to new technologies, leveraging them as opportunities for change and development.