UndocuAlly Training Programs were created across the country within higher education institutions to education people on the lived experiences of undocumented populations (Crewalk, 2021). Due to the success of such programs, a university on the East Coast implemented its own initiative, led by student-trainers (Canedo Sanchez et al., 2015). Despite the success of the program, there remains a lack of awareness about the issues that student-trainers face, who may also identify as undocumented. The purpose of this study is to examine the experiences of UndocuAlly student led trainers at a university on the East Coast and seeks to answer the following research question: What are the tensions that student-trainer’s experience as to their involvement in the UndocuAlly Training Program? Critical theory and community cultural wealth were used a framework to analyze the focus group interviews with five participants. The study revealed three important themes: (1) ambiguous loss and gain, (2) structural and symbolic violence, and (3) storytelling and counter-storytelling. This research advances understanding of the in-between spaces that undocumented students endure that impact their lives. It also serves as a resource of how educators within higher education institutions can build community resilience structures to promote positive outcomes among undocumented students, especially as they consider their transition from higher education to the workforce.