ESL learners can find it challenging to use English in a way that is pragmatically appropriate to the situation and interlocutor. In this article, we explore the impact of increased proficiency on learners' pragmatic performance. ESL learners in Australia at four proficiency levels completed three role plays, and we analysed how the learners formulated their requests. We found that the expansion of learners' linguistic repertoire with increased proficiency also led to a wider variety of request formats. Where beginner learners used imperatives and "want-statements", lower-intermediate learners added the modal "can", upper-intermediate learners introduced "could", and advanced learners used more complex expressions. Despite their improvement, learners showed little sensitivity to the social situation. We suggest ways of facilitating learners' pragmatic development through instruction.