Recent increases in high school graduation rates have been linked anecdotally to online course-taking for credit recovery. Online course-taking that supports high school completion could open opportunities for postsecondary education pursuits. Alternatively, poorer quality online instruction could diminish student learning and discourage persistence toward graduation and further education. Using quasi-experimental methods in an eight-year longitudinal study of high school online course-taking, we find positive associations between online course-taking, credits earned and high school graduation, and for those with limited online course-taking, small increases in college enrollment. However, we find significantly lower four-year college enrollments and lower-quality college enrollments for all online course-takers, leaving open the question of whether online course-taking will lead to longer-term postsecondary education and labor market success.