Calls for twenty-first-century learning design and education reform point to the need for digitally-enabled educators to be mindful of whole-person learning. The whole-person learning perspective includes recognition of the learner's life world, emotional attuning, and flexible design that gives priority to learner agency, creates space for meaningful collaboration, and promotes self and content mastery. The Community of Inquiry is a flexible theoretical framework that encourages student, peer, and teacher interaction as a fluid and complex learning alliance. At the intersection of how we think and make sense of content (Cognitive Presence) and how we demonstrate, assess, and make our learning and unlearning visible (Teaching Presence) is the visual overlap called regulating learning. This chapter is about the initial stage of an action research study regarding an open educational resource tool that helps scaffold and promote self and co-regulation within the CoI learning ecology. CoI theoretical alignment, application, and practice examples are highlighted.