In recent years, there has been an increasing interest in analyzing the linguistic features typical of various L2 proficiency levels. In the Academy of Finland project Topling, the development of writing skills of L2 learners of English, Swedish and Finnish was followed for over two years with a focus on learners’ proficiency level and their use of various linguistic structures in a number of writing tasks. This study focuses on questions used by L2 learners of English, Swedish and Finnish in email messages they were asked to write to their teachers. Findings show that there are similarities and differences in the forms and functions across the three languages and across the levels of the CEFR proficiency scale. It is suggested that at least some of the differences may be due to a complex interplay between pragmatic considerations and writers’ L2 proficiency in terms of what kind of linguistic resources they have at their disposal. More research is needed in order to further clarify the nature of this relationship.