The aim of the article is to contribute to existing research and debates on social change associated with the post-socialist transformation in Eastern and Central Europe. It does so by drawing attention to and examining the diversity of ways in which such change has been lived through and reflected upon by members of Roma (Gypsy) communities living in urban and rural environments. Drawing on ethnographic research amongst excluded and segregated Roma in the "ghettos" of Czech cities and in rural "Gypsy settlements" in the Slovak countryside, the author notes a striking difference between how members of these communities, belonging to the same extended families, lived through and reflect upon the post-socialist transformation. While the members of the Roma communities living in Czech cities perceive the post-socialist transformation as one of the most dramatic ruptures in their life trajectories, the rural Roma do not seem to have been affected as deeply and dramatically, and their life trajectories seem to be framed by different events than those directly associated with the market transition. The paper analyses and explains the social and historical conditions that (co)produce the sense of rupture or continuity in the life trajectories of members of Roma communities exposed to urban and rural environments.