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Previous research has identified the obstacles to organizing farmworkers, but we know less about why organizing endeavors succeed. For instance, Thompson (2021) underscores the experience in Vermont, and Sbicca et al.(2020) have paid attention to the work of C2C in Washington. Consequently, the strains to which farm workers are exposed do not fully explain their failure to organize. Thus, my research seeks to expand our understanding of the constraints of organizing undocumented farmworkers. I ask how the interplay between undocumented farmworkers' structural limitations and strains and the workers’ beliefs and experiences of unions and labor organizations affect organizing endeavors. Drawing on participant observation and fourteen semi-structured interviews with immigrant workers from Guatemala and Mexico, I argue that migrant workers bring a range of prior experiences with unions shaped in their countries of origin. These experiences, alongside their interactions with various workers’ organizations and their farmer employers in the U.S. These subjectivities interplay with structural and legal limitations like the fear of being fired and deported, the dispersal of the workers on countless farms in Central New York, the isolation of workers due to living on the employer's farm, and his economic responsibilities to their families in his home country. This research contributes to our knowledge about the relationship between marginalized undocumented workers and the labor movement in the US, deepening our understanding of the possibilities and limitations of a population primarily considered “unorganizable.” This paper also examines two pieces of literature that have not been previously connected: research on union renewal focuses mainly on strategies for organizing workers to overcome their preconceptions about unions, and the body of research that has demonstrated that cross-border travel experiences, transnational links, and plans can shape immigrants' willingness to participate in organizing efforts.