The COVID-19 pandemic upended students’ lives in significant ways. As college students bring their whole selves into learning spaces, these external influences created barriers to their academic success. We observed this first-hand in the undergraduate courses we taught during the pandemic. Using the lens of adaptive leadership theory, we explain how we came to understand students’ challenges and what we did to solve them. We collected data on students’ experiences through surveys, dialogue, and reflective course assignments. Analysis of this data indicated five key barriers to student academic success: technology access, difficulty learning online, adjustment to home, balancing competing commitments, and overall well-being. We discuss the role of instructors in supporting the whole student and make recommendations for practice as the pandemic continues.