Studies have shown that teacher leaders take the initiative to shape and exercise pastoral care practices to meet the rapid changes in student learning and well-being. The present study aims to examine and conceptualize the relationship between teacher entrepreneurial behaviour (TEB) and the renewal of pastoral care practices while accounting for any possible mediating effects of new technologies. We collected 446 responses to survey questions from teacher leaders from 53 secondary and primary schools in Hong Kong. We then employed structural equation modelling to test the associations between TEB, renewing pastoral care practice, and technological opportunism. The results support three proposed hypotheses insofar as higher levels of TEB are positively associated with renewing pastoral care, which is in turn mediated by technological opportunism. The results advance teacher leadership research regarding how TEB contributes to the sustainable development of pastoral care strategies in schools. They also demonstrate that teacher leaders with strong TEB are more willing to seek new technologies and treat them as opportunities for change, which contributes to the literature showing that information and communication technology (ICT) resources not only support teachers initiatives but also help them develop new ideas. Copyright © 2023 National Institute of Education, Singapore.