In problem-based learning, students work in small groups to engage with a meaningful problem or task. Problem-based learning is a form of collaborative learning in which students are actively engaged in their own learning and where the teacher’s role is to facilitate the learning process. Early in my career, I was impressed at the power of structured whiteboards and other representations to mediate their learning. This early work was with medical students who had a single instructor for groups of 4-6 students. To be able to implement PBL models more broadly, technology support holds great promise. I have spent much of my career trying to develop representations that support the kinds of interactions that inspired me. In this presentation, I will discuss how problem-based learning has been integrated into different contexts, how this has been supported with different technological tools, and what the lessons learned along the way.