This chapter examines incremental transformational learning, as evidenced by the intercultural growth of advanced learners of Russian in the Russian Overseas Language Flagship (ROF); a year-long overseas immersion program. With hybrid structured and open architecture, the ROF utilizes a scaffolded environment of individualized tutorials, small-group work, direct enrollment courses, professional internships, homestays and structured reflections. The study examines IDI- and ILR data, reporting on group-level statistical comparisons of pre/post program intercultural development and language proficiency to document measureable intercultural and linguistic outcomes. The study includes student reports of disorienting dilemmas, reflections on the dilemmas, and proposed “action plans” for dealing with challenges. IDI scores indicate a shift from a mono-cultural mindset toward greater awareness of the mindsets of others and the specifics of one's own cultural lens. The analysis indicates a positive relationship between proficiency levels and the learner's intercultural development as they are better positioned to respond and behave effectively and appropriately as global professionals.