Due to the COVID-19 pandemic, the pivot to distance learning left many higher education institutions scrambling to find the resources to shift materials online and instructors making significant modifications to their courses to adapt. This study is the critical initial step in explaining any relationships between the responsive move to remote learning and academic performance and stress, anxiety, and depression. An eight-month longitudinal cohort study design with an action research methodology was conducted over four waves from June 2020 to January 2021. Participants had the option to be involved with semi-structured, in-depth interviews via Zoom. The qualitative results from the in-depth themes include: health & wellness, relationships & connectedness, transition home, classroom changes, learning & participation, extra-curriculars, COVID-19, virtual challenges, academic performance, and self-regulation. Thus, through thoughtful and intentional accommodations, instructors and students may create a new digital space for learning to improve upon motivational barriers and retaining content.