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Sociologists have explored the benefits of intentionally designed transfer partnership alliances for facilitating the success of transfer students. The aim of this study was to understand how students who move from a 2-year to 4-year institution with and without the support of a transfer partnership program describe their transfer experiences and the degree to which cultural capital was required to navigate this transition. A basic interpretive qualitative analysis of 28 interviews was conducted using open coding methods adapted from grounded theory. These analyses compared 13 students who took part in a transfer partnership program with 15 students who transferred to the same 4-year institution without the support of this program. Participants from the two groups described their transfer experiences in very different ways. Those who took part in the transfer partnership program perceived a streamlined transition that alleviated the need for cultural capital in the form of preexisting knowledge of transfer processes. By contrast, students who transferred without the support of this partnership program described their experiences as more arduous, filled with unexpected challenges that disproportionately impacted the experiences of first-generation college students. Notably, transfer partnerships did not eliminate inequality based on generational status; instead, evidence suggests certain challenges may reemerge as students begin upper-division coursework following program completion. These findings demonstrate the ways transfer partnerships can help to alleviate inequality between students based on generational status. Implications for research and practice are discussed.