Since Estonia joined the European Union in 2004, there has been a steady growth in transnational mobility for work or study among Estonian young adults, a phenomenon further boosted by the economic recession of 2008–09. This article analyses the factors that have influenced or would potentially influence their return to Estonia, following an online survey of over 2,000 participants from Estonia aged 20–35 years with a recent experience of living abroad. By deploying an analysis of logistic regression, we developed two models concerning the ‘actual return factors’ (comparing the stayers with those who have returned) and the ‘aspirational return factors’ (how the migrants imagine their future location). Some of the highlights of our results demonstrate that the likelihood of return migration is significantly lower for those whose prime reasons for leaving Estonia were related to living conditions and salary abroad. The extent of people’s ties and connections to Estonia does not play a significant role in actually returning to Estonia. However, these connections do play a role, albeit limited, in envisioning one’s future in Estonia. The outcomes of our analysis suggest that diaspora policies cannot be implemented without addressing the sending country’s internal sociopolitical situation, which influences the living conditions and economic opportunities of its citizens, scrutinized particularly carefully by those who have left the country before deciding whether or not to return.