The Mexico–U.S.A. border is one of the most active borders in the world, with many migrant men traveling to the United States to serve as “breadwinners” for their families. Yet knowledge within psychology is limited regarding how Latino migrants’ masculine identities may be shaped within the migration context as most studies are set within the United States. This gap in the literature continues to exist despite many Latino migrant men’s engagement in transnational lifestyles involving multiple migrations between their country of origin and the United States. A more complete investigation of all phases of the migration journey, including return-migration, is then vital in the understanding of migrant men’s experiences. Guided by gender strain theory and transnational conceptual frameworks, we used case study methodology to examine masculinity among return-migrants in Petlalcingo, Mexico to understand how migration-related life events relate to masculinity by identifying key moments and turning points within their migration process, such as: the decision to migrate, the migration journey, adjustment and acculturation in a new country, and return-migration. Findings elucidate a gendered migration process as well as key variables that can be utilized in the development of larger binational studies examining masculinity and migration.