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Research has demonstrated that attending a selective college increases the probability of graduating and accessing certain economic and social opportunities, but few community college transfer students obtain such an opportunity. In an effort to seriously consider how to increase access to this underserved population, it is important to examine the bridges by which academically-qualified community college transfer students access selective institutions. This multi-case study looks at why and how three private selective institutions in Massachusetts currently recruit community college students. The four main themes identified as to why these institutions recruit community college students were: strategic enrollment practices, diversity, institutional enrichment, and community engagement. The two themes identified for how institutions recruit community college students were: information sharing and infrastructure support. Several challenges facing both the selective colleges, and the community college transfer students were also identified and explored. The major finding of the study was that the unique position occupied by each institution within the hierarchy of the higher education system influences the rationale as well as the methods by which it approaches and considers the transfer of community college students.