This longitudinal study asks 2 questions. The first one is: What patterns of pragmatic development can we observe among different pragmatic functions and attributes in a second language (L2)? The second question is: In what ways do individual differences and learning context affect the course of pragmatic development? Forty-eight Japanese college students studying English in an immersion setting in Japan participated in the study. They completed a pragmatic speaking task (k = 12) that measured their ability to produce 2 speech acts, requests and opinions, in 2 situation types: low-imposition and high-imposition. The task was administered 3 times over 1 academic year. Gains in the appropriateness of the speech acts and fluency of production were analyzed. In addition, a subset of the participants was interviewed to seek the relationship between pragmatic gains and types of sociocultural experiences available on campus. Results revealed that appropriateness showed a profound increase for the low-imposition speech acts, but the production of high-imposition speech acts was slow developing. There was a large increase in speech rate at the initial stage for both situation types, but it showed stagnation at the later stage. Qualitative data revealed an interesting portrayal of the learners' history of participation and socialization related to pragmatic development.