This paper explores a teacher leadership development programme initiated by a university-based educational innovation centre that convened 40 teacher leaders from 22 different school districts across Florida for an 18-month voluntary professional learning experience. Underpinning this initiative was a theory of teacher leadership development aimed at developing a culture of professional learning at individual teacher, school and district level. It was designed to challenge, at both school and district level, a perceived ambivalence among senior leadership to teacher led-initiatives aimed at enhancing the professional knowledge and skill of their colleagues. Findings indicate that participation in a university-sponsored programme, as well as developing collaboration among teachers, served to promote a commitment to teacher-led leadership. Further, the researchers identified specific strategies which would encourage Fellows to explore new areas of learning. This also entailed confronting obstacles and disincentives employed by teaching colleagues and senior leaders at both school and district level. This article explores not only the conditions and practices that shaped the programme but also the larger contextual factors that determine when, how, and if teacher leaders are able to exercise leadership.