Professional development in information and communication technology (ICT) remains a major imperative for schools as technologies, and what teachers are able to do with them, continue to evolve. The responses of individual schools to this ongoing challenge can be highly diverse and inevitably shaped by past and current cultural practices, which include the values, attitudes and beliefs of school leaders and teachers themselves. This paper provides case study data from seven schools, drawing attention to the diverse ways in which individual schools approach teacher learning and providing a stimulus for educational leaders to reflect upon how the histories and cultures within their own schools may enable or constrain change in relation to ICT use. Informed by complexity theories, the paper argues that a focus on the complex, nuanced, social dynamic of ICT professional learning within the whole-school context is critical in supporting change surrounding ICT integration. (Contains 3 tables.)