This chapter examines key factors that lead to failed democratization. It first describes five categories of countries: established democracies, established autocracies, robust democratizers, tenuous democratizers, and failed democratizers. Using the Freedom House Index, it explains why some democratizers slid backwards while others did not. In particular, it looks at the conditions that undermine democracy and political actors, such as the chief executive, that contribute to democratization’s derailment. The chapter identifies several major structural factors that influence whether democratization succeeds fully, succeeds partially, or fails. These include poverty, a late history of national independence, a large Muslim population, economic reliance on oil and gas, and gender inequality. The chapter concludes by considering ways of reducing the hazards of democratic reversal and preventing relapses into authoritarianism, such as strengthening legislatures and curtailing executive power.