A study of hidden risks, anxieties and barriers to STEM student transfer from community college to a large, comprehensive university is presented. This qualitative study employed a thematic analysis of student responses to a semi-structured interview that asked students about their hesitancy to transfer to a 4-year institution. Participants included students enrolled in a collaborative NSF-sponsored S-STEM scholarship project between three community colleges and a large public university (all in the same large metropolitan area). The project included elements that are well documented in the literature to encourage transfer. These include advising visits by university staff, clear articulation pathways, scholarship support to assist with costs, peer and near peer mentoring opportunities, and cohort-building activities between campuses and on each individual campus. Transfer rates in this group were higher, but still many students with declared interest in transferring did not transfer on time or at all. The authors identified numerous hidden risks and barriers to transfer, in addition to the well-known ones found in the literature. These include additional academic, financial, social, logistical and external/family related barriers. A theme common to many of these barriers was complex bureaucratic processes and events outside of student's direct control. Many student comments highlighted the importance of in-person connections, mentoring and advising.