This paper reports on the theoretical underpinnings, design, and initial findings of a research project funded by the US National Science Foundation´s Cyberlearning Program. At the epicenter of the project is the use of digital ink both in collaborative 'what you see is what I see” workspaces to reshape the nature of flipped classrooms, and in creating interactive digital media, especially videos, used as lessons for the flipped arrangements. In addition to pen-based computing, flipped classrooms, collaborative workspaces, and digital media making, the project deploys help-giving software agents. The purpose of creating the ensemble is to understand the interaction between enabling technologies that can contribute to highly immersive and high-performance learning settings. The classroom ecosystem this ensemble produces appears to foster significant development across multiple accepted categories of social and emotional growth in service of academic learning. For that reason, the focus on learner engagement has expanded to include these growth areas.