The boundary of uncertainty is at the edge of what a learner can do without help. At this boundary, a learner can only succeed by collaborating with someone who has a broader knowledge, experience, or skill set. When someone supports an uncertain learner, the moment is termed a touchpoint. Touchpoints are important; relieving a learner’s struggle too soon does not produce learning results and relieving them too late causes frustration that is counterproductive to learning. This paper discusses the uncertainty boundary in terms of collaborative design projects in which mentors use student-created artifacts to purposely pull a learner to a series of “need to know” places. These places indicate the boundary of the learner’s independent ability. Successfully completing these projects requires the learner to connect with peers, mentors outside the specific course, and outside the academic environment, each with specific knowledge, experience, tools, and skillsets. We further discuss the advantages of extending this “need to know” impetus across course boundaries in a collaborative teaching environment and the struggles of implementing a more complex collaborative design project.