Our study draws on an investigation of Sweden’s participation in the European Union Strategy for the Baltic Sea Region (EUSBSR) to ask what it can reveal regarding how ‘awkward’ states in regional integration – those regularly considered by their partners to be beyond the regional mainstream – can secure their preferences nonetheless. We test the independent variables of ‘awkwardness’, by focusing on the ongoing work of officials charged with making the EUSBSR work in practice. We thereby seek to add to existing macro-level analyses of Sweden’s place and position in the European Union that tend to focus on ‘big picture’ matters. Our findings suggest that Swedish actors working within the various agencies and institutions associated with the EUSBSR have been able to offset their country’s perceived awkwardness by developing a reputation for everyday effectiveness and reliability. This leads us to the tentative conclusion that under certain conditions awkward states can offset this status, and, in the words of the everyday metaphor, have their cake and eat it too.