Ever since its independence (1991) and up until the present day (2019), the Republic of North Macedonia has been interested in becoming an EU member state. Recently, however, this pro-EU aspiration has been challenged by anti-EU sentiment due to a string of events, unfolding over two distinct periods. These include: (1) the past societal trauma (1991–2006) and (2) the consequences of a decade-long rule by a right-wing party culminating with a wiretapping scandal and followed by an increased international presence during management of the crisis (2006–2017). In addition, the stagnation of the EU accession process (2005–present) and the referendum for the change of the country’s name as one of the conditions for the start of EU negotiations (2018) also played a considerable role in the interplay between pro-EU aspirations and rising anti-EU sentiments. Together, these factors provided fertile ground for the appearance of EU-related conspiracy theories. This chapter offers theoretical considerations and some empirical findings related to a host of conspiracy theories emerging in the current Macedonian context and targeting the international community. Specifically, it provides insight on the political, social, and psychological factors that may instigate or hinder their further expansion.