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As a region that is simultaneously demilitarised, neutralised and autonomous, the Åland Islands represent a unique and long-established case in international law. However, this status was never independent of surrounding events. The early 1990s saw both the end of the Cold War and Finland’s accession to the European Union. This paper offers an analysis of the discussion regarding Åland’s demilitarised and neutralised status among both Finnish and Ålandic legislators during this period. It finds that Finnish policy-makers saw little need to discuss the matter. Åland’s officials continuously criticised the Finnish Defence Forces’ presence in the region as excessive and proved unwilling to let the issue rest. Against formal obstacles, they established themselves as a relevant actor, facilitated by differing approaches of political, diplomatic and military officials in Finland. Other sovereign states showed only limited interest in the discussion, making it a domestic one for the most part.