Based on a widely held belief that immersion provides the best language learning opportunities, a large number of Asian students go to English-speaking countries to improve their English language skills. These strongly motivated learners arrive in a new country with a bag of expectations, learner beliefs, and imaginations about the new community they are about to enter. However, learners are often faced with a set of challenges with respect to language learning opportunities and identity negotiations in the new community. Against this background, the present study examined three cases of Korean learners enrolled in an intensive English program (IEP) in the U.S. The aim of the study was to understand distinct struggles experienced by this learner population. The study found that the participants had certain motivations and imaginations about the new communities, but they experienced numerous challenges and struggles particularly with regard to opportunities for authentic communications in English and identity conflicts. The paper discusses pedagogical implications for an effective IEP curriculum to allow students more opportunities for legitimate periphery participation in the target language communities of practice.