The Åland convention of 1921 established demilitarization and neutralization as means of stabilizing the security order in the Baltic Sea Region. Following Finland´s and Sweden´s accession to NATO, the strategic environment of the region has changed significantly, raising questions about the relevance and interpretation of this long-standing security arrangement. This study examines how the strategic significance of Åland and the role of the convention are represented in political media discourse in connection to the NATO enlargement. Using Bacchi´s “What´s the problem represented to be?” (WPR) approach combined with perspectives from strategy, norm, and securitization theory, the study analyzes discursive effects. The findings indicate two dominant representations: Åland as a strategic vulnerability and Åland as a normative asset. These competing discourses shape how military planning, legal commitments and political legitimacy are understood in the evolving Baltic Security order.