The COVID-19 (coronavirus disease–2019) pandemic disrupted the education of students across the globe in the spring of 2020. Students who were previously at most risk for falling behind their peers and through the cracks because of academic, financial, racial, and/or generational disadvantage faced a wide range of additional obstacles in the pursuit of their college goals. This qualitative study sought to uncover postsecondary advising implications for students through the perspectives of near-peer college advisers (n = 23) serving in high-need schools in two different states as intensive, in-person advising was forced to adapt to virtual formats. Two key thematic findings reveal that advisers faced new communication challenges and existing systemic barriers for marginalized students became even larger. For seniors who had not yet made final postsecondary decisions or who had remaining to-dos, the impact of school closures and distanced advising may have fatally widened existing cracks in the path to college.