The recent COVID-19 pandemic has forced many institutes of higher learning across the globe to consider alternative modes of providing quality learning for students. However, developing and implementing safe spaces for academic advisement in online platforms that allow college students to explore their environment in an open and curious manner is challenging. The view that unsafe spaces put college students at risk for departure if they experience disengagement and a lack of support led this paper to explore how college students make sense of safe and unsafe advisement spaces, and how this understanding affects the ways they achieve academic success. Utilizing the PALEO framework, this paper contributes to existing knowledge on academic advisement by theorizing and offering practical ways to create tools that extend the capacity to solve problems during a global pandemic. The implications for re-imagining and coping with this new normal is discussed.