The promotion of teacher entrepreneurial behavior (TEB) is important for advancing educational change and innovation in schools. However, the principals’ role in facilitating TEB has not been conceptualized in the context of educational leadership theory. This study investigates teachers’ perceptions of principal leadership in cultivating TEB. Using a case study approach, we show how entrepreneurial teachers actualized innovative school-based curriculums in three successful schools. Several principal leadership practices were found to support the teachers when performing TEB. These results further underscore the use of connective pathways by principals for empowering entrepreneurial teachers. Copyright © 2022 Taylor & Francis Group, LLC.