This article addresses the challenges and pathways of Holocaust education in post-communist countries through two case studies. I first examine historiographical, institutional and cultural obstacles to deep and meaningful treatments of the Holocaust within Latvian and Romanian schools. Drawing upon the unique experiences both countries had with partial or full ‘dual occupation’ of Nazi Germany and the Soviet Union, I present a rationale for constructing inquiry-based Holocaust education experiences. As Latvia, Romania and other countries have entered the European Union, the need for tolerant and open-minded citizens who have the ability to make informed and reasoned decisions for the common good has become more critical. Inquiry-oriented teaching of the Holocaust brings about essential democratic skills and dispositions, while simultaneously positioning students to investigate the complicated, nuanced and contested contours of the Holocaust, competing forms of propaganda and often spurious historiographical traditions. This kind of teaching is also responsive to the challenges these and other societies face when confronting other historical and contemporary controversial topics.