The shift to remote learning at UCalgary during the COVID-19 pandemic was difficult. As members of the Teaching and Learning Subcommittee of the Campus Mental Health Strategy, we believed it was important to explore students’ mental health and learning experiences during Winter 2020 to inform the development of strategies to support their online learning and wellbeing in Fall 2020. For Part 1, over 300 students were surveyed about their experiences with remote learning during Winter 2020. These responses were used to develop eight recommendations for instructors for online course design and to create seven wellbeing self check-ins that were distributed to Faculty of Arts’ students throughout Fall 2020. In Part 2, students were invited to complete a follow-up survey about their online experiences in Fall 2020. These results (N = 60) were used to improve the wellbeing check-ins for Winter 2021 and better understand students’ needs during online learning.