Engagement through the use of technology requires a level of vulnerability and trust amongst teachers and learners. The emotional and social aspects of engagement can be significantly affected by the nuances of the learning setting. The study goal was to explore learner needs related to uploaded lecture-captured recordings and examine how the use of a commenting feature might enhance learning experiences. Building on self-determination theory, we postulated that affording commenting opportunities would increase engagement (relatedness), with learners choosing to engage in the potential learning value from comment over the vulnerability that could come with making public comments (autonomy), and improved learning outcomes (competence). Using a pre/post survey design, 100% (N = 190) of second year undergraduate medical and dental learners participated in this study. Pre-survey results demonstrated that 65% (n = 94) perceived value in seeing what others asked; 59% (n = 94) of participants wanted to view the responses of others. Post-survey results demonstrated that 6% (n = 12) indicated that commenting made them feel vulnerable. Twenty-nine percent (n = 55) preferred anonymous commenting. Engagement was impacted by technical issues with the new system, learners not perceiving significant 'value-add' due to alternative mechanisms in receiving answers to questions, and the timing of our technology change. Learners still perceived value in creating opportunities to ask questions and seek responses, though it must be balanced with ensuring that the learning environment allows vulnerability. Meaningful connections can be found in various ways throughout the learning environment in both the formal and parallel curricula.