The present study explores the process of how Korean students develop pragmatic competence when writing request emails during metapragmatic instruction. In particular, the study focuses on how students’ usage of request strategies, lexical devices, external modifications, and request perspectives change during the metapragmatic instructional period. Descriptive analysis of the usage frequency of politeness devices was conducted to examine changes before and after the instruction. In addition, the participants’ accounts during the metapragmatic discussions and retrospective interviews were analyzed to ascertain their intentions of the requests as well as their experiences during the instructional period. The results of the study showed that the participants developed pragmatic competence as they enhanced their awareness of the difference between what they had intended and what was actually conveyed. Moreover, the metapragmatic discussions among their peers in regard to the source of the pragmatic failure as well as their developing pragmatic awareness allowed them to experience meaningful interactions. The study stresses the need for explicit metapramatic instructions along with encouragements for metapragmatic discussions to reflect on the norms of the target culture along with their own pragmatic knowledge for Korean students to enhance their pragmatic competence.