There is growing interest about the concept of Open Educational Resources (OER) and how it can transform education around the world, with governments exploring the potential of OER and considering policy positions supportive of open licensing. The urgent imperative--and the real transformational potential of OER--is to evolve new systems of education that can help societies, and especially youth, to navigate their way through a world in which the disruption wrought by information and communication technologies (ICT) requires a completely new approach to knowledge, skills, and competence. Ubiquitous access to open content offers an opportunity to re-think the basis on which educational experiences of school students are organized and to liberate the time of teachers so they can focus on providing meaningful support to students rather than continuing to act predominantly as conduits of information from the textbook to the students. This provides an opportunity to overhaul resource use and the nature of teacher-student interaction so that students can develop key attributes required for success in the knowledge society. This paper thus seeks to engage with the challenge of determining the conditions under which use of OER can drive a transformative educational agenda in schooling systems. It considers two key emerging questions: (1) What role can OER most effectively play in supporting school-level pedagogical transformation? and (2) Given the inherent conservatism in public schooling systems, what policy approaches may most successfully initiate such transformation? In exploring answers to these questions, the authors initiated two action research exercises: one at the school level at a private school in Johannesburg, South Africa; and the other at a national level in Antigua and Barbuda.