Studies that have measured pragmatic fluency in the form of planning time and speech rate, as indicators of processing ability, have confirmed that learners' processing ability and pragmatic knowledge are independent from each other. The present study is a longitudinal, developmental investigation which investigates whether the study abroad stay (SA) has an effect on the overall appropriateness, planning time and speech rate in high and low imposition situations of ten L2 Japanese learners' oral requestive output during their overseas sojourn. With the exception of appropriateness which had the most positive change, (mainly with low imposition requests), the study found that the SA had minimal positive impact on the variables examined, suggesting that activation and processing of pragmatic knowledge needs enhancement from other sources, and that learners need a longer period of time to develop appropriate pragmatic output across a range of academic encounters. Results further revealed much individual variation, further highlighting the complexity of examining pragmatic performance over time.