What explains varying levels of emigrant transnational engagement in homecountry politics? The well-known difficulties in obtaining migrant profile data and restriction to a few destination countries have resulted in a lack of systematic empirical investigation of this question. We expand nascent efforts to fill this gap by offering a new theoretical framework and novel research design that stress the potential importance of destination characteristics. We argue that the experience and environment in emigration are critical factors for emigrants’ engagement with two major types of homeland-related political activities: electoral and community. Using Ukraine as a case of an average migrant-producer developing country and using count models on original survey data on Ukrainian extraterritorial voters in a diverse set of 15 countries, we show that assimilation, emigrant networks, and destination characteristics are consistently strong predictors of transnational political engagement among the emigrants who show at least a minimal concern for homeland politics.