The European Union’s ambition to create a harmonized reception system for asylum seekers differs from the realities on the ground. We address how differences in national reception conditions stimulate the secondary migration that challenges the creation of an effective common migration regulation in Europe. We base our analysis on the Dublin Regulation (DR) and the secondary movement of Eritrean asylum seekers from Italy to Norway. The empirical material consists of qualitative interviews with civil servants, NGO representatives, and Eritrean migrants in Milan and Rome, and Norwegian civil servants. Recently developed models of migration destination selection were used to analyse the interaction between individual aspirations and structural constraints. We found that the Eritrean informants remained highly motivated to apply in a second country but were to some extent held back by the DR. Supranational regulations were challenged by the migrants’ actions and by national differences in reception and welfare standards. Both the migrants’ aspirations to move on and the challenges to a harmonized regional regulation of migration increased during times of economic crisis.