Located in between, but separated from, the mainlands of Finland and Sweden, the Åland Islands have for a century negotiated complex relationships of politics, language and culture with both regions. Åland is an autonomous territory of Finland but its language base is distinctly Swedish rather than Finnish. Technically, Åland’s single official Swedish language is protected by the Finnish constitution and even a ruling of the Council of the League of Nations. But Ålanders have long feared incursions from Finland that might erode the protections for Åland’s Swedish speech. In the academic literature these fears have largely been addressed in terms of the legal competences held by Åland as an island territory and/or the politics that drive Åland’s relationship with its metropole Finland. This research note shows that the Swedish language in Åland may be at threat from a novel angle, namely shifts in both language and imagined community that can occur in the wake of changing global business relationships. To explain this threat, the research note explores the corresponding shifts that have transformed the remote and formerly bilingual region of Madawaska in the northeast United States. Although from a distant location – geographically, politically and culturally – this story of Madawaska stands as an important and potentially controversial cautionary tale for Åland.