This longitudinal qualitative research case study analyzed how international students in their first semester at an intensive English program (IEP) managed their English language learning experiences while transitioning to a new academic learning environment. Their experiences of cultural and educational transition were viewed through the lens of self-regulatory learning habits and behavior. Three linguistically and internationally diverse students who identified as highly self-regulated learners through Likert-scale questionnaire responses were interviewed at the beginning, middle, and end of their first semester at a large university-affiliated IEP in the western part of the US. The three students came from Central America (Spanish speaking), Sub-Saharan Africa (Malagasy & French speaking), and Asia (Mandarin Chinese speaking). Semi-structured interviews yielded data about what self-regulated learning (SRL) principles and practices the students brought with them to the IEP and which SRL principles and practices were maintained, newly developed, or not used throughout their first semester. Data collected from the semi-structured interviews about their transition experiences were organized and analyzed within a six-dimensional model of SRL that included how students managed their motives, in-class and out-of-class learning methods, time, physical environments, social environments, and language performance. Implications for researchers, administrators, and teachers are discussed, including the role of resilience as an important self-regulated learning practice for language learners.