The dual aim of this article is, on the one hand, to identify Bessarabian writers’ individual and group rationale to stay in the territory occupied by the Soviet authorities after 28 June 1940 and, on the other hand, to analyse the institutional mechanisms set up by the Soviet authorities (namely the Moldovan Writers Union (MWU) and AgitProp) to integrate these writers into the Soviet cultural system. The three groups of Bessarabian writers remaining in the annexed territory (the ‘regionalists’ from Viaţa Basarabiei journal, the writers of Jewish origin and the formerly ‘underground’ (pro-Communist) activists) intersected and overlapped, since the writers’ interests were often multiple. At the same time, the strategies implemented by the Soviet authorities to enrol Bessarabian writers into the Soviet institutional structures followed a binary and apparently contradictory rationale, of inclusion (of candidates deemed suitable for the aspiring status) and exclusion (of those who did not correspond to the criteria of political probity). Moldovan writers coming from the Moldavian Autonomous Soviet Socialist Republic (MASSR) (the ‘Transnistrians’) had a crucial role in the integration and enrolment of Bessarabian writers into the MWU as mediators with the Soviet authorities (having had a longer ‘length of service’ in Soviet political and cultural affairs), as well as in the role of cultural and ideological ‘tutors’. In response to these enrolment strategies operated by the MWU, Bessarabian writers adopted a zealous and emulative behaviour in order to ensure their successful integration. This behaviour laid the basis for duplicitous and somewhat dysfunctional interactions between writers, which would reach a paroxysm in the post-war ‘Zhdanovist’ campaign.