This chapter examines extreme cabinet militarization under former President Jair Bolsonaro. It argues that this militarization can be attributed to a combination of Bolsonaro’s preferences, the ideological and material motivations of the military, and political elite support. Permissive conditions such as presidentialism, declining party system institutionalization, and high public trust in the military set the stage for this phenomenon. The chapter discusses the involvement of military officers in civilian roles, comparing this to historical precedents in Brazil and other Latin American democracies. The chapter traces the causes of the military’s renewed political influence, distinguishing between permissive and proximate conditions. It also discusses the limits to militarization, emphasizing the armed forces’ commitment to democracy. The chapter concludes by contextualizing Bolsonaro’s militarization within the broader trends of civil–military relations in Brazil, offering insights into the potential implications for democratic stability.