The current study investigates students’ beliefs about the role of context in the acquisition of grammar, vocabulary and reading comprehension skills. Participants included 78 non-native speakers of English with similar L1 backgrounds. They comprised two groups according to their English learning in one of two learning contexts-an at-home university (AH) in Taiwan and a study-abroad (SA) setting in the Midwest United States. The study compares the acquisition of English skills observed through the Michigan Test of English Language Proficiency (MTELP). The purpose of the study is twofold: (1) to shed light on the assumption that studying in the target language context is the best way to improve various aspects of language learning, (2) to compare students’ beliefs about language learning and the role of context in their linguistic development. The first purpose was investigated through a pre- and posttest, approximately six months apart, using the MTELP, which measures knowledge of grammar, vocabulary and reading comprehension. Two focus groups were formed for the second goal of the study, one group from each learning context. The two groups participated in interviews based on their perspectives of the learning context and their L2 learning. Preliminary findings showed that SA students improved in all areas, but results were statistically significant in vocabulary, which equaled a gain in total test scores. This gain is attributable to a combination of intense coursework, active and natural learning processes, time of interaction, and self-initiated efforts. Comparatively, the AH students decreased in all areas except reading, but showed statistically significant decreases in grammar and vocabulary because of lack in intense coursework, passiveness in learning, limited time of interaction, unwillingness to study after intense standardized testing, and lack of self-initiated learning and interactive out-of-class contact. After primary analysis, main findings uncovered three main trends in data: (1) extended L2 exposure while in the SA context is needed to accumulate sufficient gains in grammar while SA vocabulary is quickly acquired, (2) the successful English magazine industry of Taiwan has arguably led to the marginal gain in AH reading comprehension, the only improved skill in the AH context, and (3) although students had deep perceptions based on their learning experiences, their beliefs often conflicted with the reality of their achievements. The entirety of these findings demonstrate the importance of having a strong relationship between what the context offers and how the student utilizes these offerings interactively. Nonetheless, the circumstances are ever-changing for stakeholders in education and so is the need to investigate contexts from in-depth comparative angles.