This study explores the unique characteristics and experiences of ten undocumented male Mexican immigrant students, with their resiliency and ambiguous journey as they encountered and transitioned into higher education. Five of the students attend a community college; two attend Texas State University San Marcos; and three attend a University of Texas System. Five phases of their transition are revealed: their characteristics (born and raised), journey from Mexico to the Untied States, the development of resiliency, the ability to confront and deal with ambiguity, and the resourcefulness to maintain their identity. In addition, a developmental model of immigrant resiliency was derived from the five areas explored. Within the study, the participants were asked to reflect on the support and barriers that they encountered which influenced their educational goals and aspirations.