The chapter addresses pragmatic features in the speech of highly proficient Swedish users of L2 English, French, Italian and Spanish in comparison with native speaker production. Three domains of pragmatic competence representing an increasing scope are the focus: use of pragmatic markers, implementation of specific speech acts, and variation with regard to socio-cultural alignment. Two aspects are highlighted: which is the role played by transfer in L2 performance, and which of the three domains represents the strongest challenge to the learner. Results concerning pragmatic markers show that, although sophistication increases with higher proficiency, the level of native use is hardly ever attained even in near-native users. Regarding speech acts, the L2 users closely resemble their native counterparts, except in one respect: the L2 users tend to make less conventional choices. With regard to socio-culture, alignment to native speaker behaviour clearly increases with cultural proximity. While transfer stands out as an essential factor in explaining how high-proficient L2 users deal with the pragmatic challenges of their target language, no support can be lent to the hypothesis that high-scope domains are less effectively acquired than low-scope domains.