The present exploratory study evaluated perceptions of actual support received in relation to stress and well-being among first-year students attending Canadian and U.S. higher education institutions (N = 126). Given that traditional assessments of received support account only for how often support was received, the present research examined unique effects of support quality in addition to frequency with respect to four distinct sources of support (family, friends, faculty/staff, institution). Following from empirical confirmation of received support frequency (RSF) and received support quality (RSQ) as distinguishable constructs, RSQ was found to significantly mediate effects of RSF across varied well-being outcomes (e.g., stress, burnout, quitting intentions) in relation to family, faculty/staff, and institution support. Overall, study findings highlight the importance of evaluating the quality of support received by first-year students during the transition to higher education and show faculty/staff support to be an important contributor to student well-being.