Much public discourse surrounds the intractable problem for some community college students in attaining a bachelor's degree through vertical transfer. Scholars have found 80% of entering community college students plan to transfer, yet this intent to transfer is somehow diverted for most (Jenkins & Fink, 2016). Although a new report showed an increase in vertical transfer for community college students (Dembicki, 2024), previous statistics have remained stubbornly fixed, with only 17% of community college students transferring and attaining a bachelor's degree within 6 years successfully (Jenkins & Fink, 2016). Broken transfer pathways disproportionately affect low-income and underrepresented students who populate U.S. community colleges (Jenkins & Fink, 2016). Scholarship has similarly aimed at understanding the barriers for low-income and underrepresented students who, despite evidence of academic ability, are less likely to transfer to selective colleges than their peers (Dowd et al., 2008a; Glynn, 2019; Rosenberg & Koch, 2021). Recognizing the role advisors play in supporting transfer student success, this qualitative study sought to understand how community college advisors cultivated practices that saw them considering power, privilege, and bias in themselves and others. Using Brookfield's (2017) theory of critical reflection, this study considered how community college transfer advisors' social identities (i.e., positionality) informed their advising interactions; how community college transfer advisors cultivated critical reflection in their advising interactions; and how community college transfer advisors understood the connection between critical reflection, advancing social justice, and emancipatory thinking in advising interactions. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]