As the new democratic republics of Eastern Europe experience sweeping transformations in their political, economic, and social institutions, their educational systems must also undergo changes to address the new roles and responsibilities of citizens. The purpose of this article is to explore the impact of these changes in two specific contexts, Lithuania and Macedonia, by drawing upon research conducted in conjunction with two projects in which the author has recently been involved, one at Vilnius Pedagogical University in Lithuania, and the other at South East European University in Macedonia. These studies, by utilizing questionnaire responses from education students at these institutions, address the challenges being confronted as educators in these countries seek to create educational systems and teaching practices that support democratic values and participatory citizenship. Although the studies were conducted separately and the contexts and specific issues differ in each setting, their findings reveal some commonalities and differences concerning the struggles that educators encounter, particularly regarding the role of schools as sites for promoting democracy. (Contains 17 endnotes.)