This brief is one in a series aimed at providing K-12 education decision makers and advocates with an evidence base to ground discussions about how to best serve students during and following the novel coronavirus pandemic. It addresses one central question: How can research inform student transitions from high school to college and career, given the financial and health uncertainties that students -- particularly those who are marginalized and traditionally underserved -- are facing due to the COVID-19 pandemic? In order to answer this question, the brief breaks down the issue into three points: (1) Recent recessions have increased existing employment gaps between workers with and without a college degree; (2) Research generally shows that students are better off attending college versus not and better off attending a more selective bachelor's degree-granting institution; and (3) Both college-bound and career-bound students are at risk of losing momentum in 2020-2021 and transitioning to a less secure postsecondary pathway. Based on these points, the brief provides four strategies to consider and two strategies to avoid. [This brief was co-prepared by Southern Methodist University, Simmons School of Education & Human Development.]