Research has both established that developing teacher capacity is a key to educational reform and that leadership plays a significant role in promoting teacher learning. Yet, despite education reforms that focus on teachers and teacher development, Thailand has yet to strategically utilize school leaders as the bridge between its ambitious vision and school enactment. This study examined differences between effective and ineffective school leadership practices aimed at advancing teacher learning in Thailand. Drawing upon data from a larger mixed methods study, this article employed a contrasting groups design to examine differences in the leadership and teacher learning practices in two rural secondary schools. In addition to semi-structured interviews with principals and teachers, qualitative data were also gathered from school web sites, Facebook and administrative documents. The results illustrate that, given a similar set of situational challenges, principal's viewpoints, principles, purpose, and actions can make a difference in catalyzing, supporting, and sustaining teacher learning. The case studies show how learning centered leadership practices (or lack thereof) can shape teacher learning and contribute to a growing body of research on learning-centered leadership.