This chapter explores how Estonia’s self-perception evolved in relation to Europe during the Soviet years and the re-establishment of its independence. It focuses on co-articulating the ‘Soviet question’ with the ‘European question’, examining how decades of Soviet rule impacted the understanding of Europe and Europeanness in Estonian national imaginaries. This analysis considers various factors, including the understanding of Europeanness before the Soviet era, the Soviet colonial matrix of power, changes within the USSR, the orientalization of Eastern Europe in West-European imaginaries and the influence of Soviet state-promoted ideologies on local cultural imaginaries. To address these complex issues, a multi-scalar understanding of social phenomena is employed. From this perspective, Estonia’s geopolitical shift from the Soviet West to the European East during its re-establishment can be seen as a shift in the geopolitical scale-system. Generally, attention to scale as a ‘tool for bounding space at different geographical resolutions’ allows us to perceive historical conditions as complexly multiscalar. A multiscalar approach reveals how meaning-making unfolds through interactions across different scales of sociopolitical realities and imaginaries, showing how local, regional and global scales formed complex and dynamic systems of interdependency in Soviet-era Estonia.