The chapter examines how ten Central and Eastern European (CEE) countries moved from late socialism through democratization, market transition, and EU accession and how these shifts have shaped crime trends and penal policy. After 1989, constitutional reform, Council of Europe and EU requirements, and expert-led discourse produced less punitive, more rights-oriented penal systems: death penalties were abolished, imprisonment was reframed as a last resort, and community sanctions expanded, with falling prison populations in many states. At the same time, regime change generated severe social dislocation, rising inequality, corruption, and new forms of crime, which gradually eroded early optimism. The chapter also discusses crime trends, changes in the structure of crime, and incarceration rates. The chapter concludes that a persistent “penal gap” separates East and West despite decades of legal and institutional convergence. In CEE, incomplete Westernization, socialist legal legacies, deep socio-economic inequalities, weak civil society, and populist governance all support more punitive penal policies and higher incarceration. Early post-transition moderation gave way to “authoritarian crime governance within democracy”, especially in Hungary, Poland, Serbia, Bulgaria, Romania, and Bosnia and Herzegovina (BiH). Echoing Dahrendorf, the chapter argues that while political and economic systems can change relatively quickly, the civic culture needed for stable, moderate penal policy may take generations to develop, which helps explain why many pre-transition features – most notably high prison rates – endure.