Separated from Tunisia by only 75 nautical miles, Sicily, the southernmost region of Italy, was the first Italian region to experience Tunisian migration in the late 1960s. Despite being economically marginal to Italy, Sicily also has a history of extensive economic and political relations with Tunisia. This paper examines the changing condition of Tunisian migrants in Sicily focusing on two periods of flourishing cross-Mediterranean relations: the first half of the 1980s (mainly in association with the fishing sector) and the first decade of the 21st Century (mainly characterized by EU cross-border cooperation subsidies). Drawing on a combination of oral histories, interviews and archival research, the paper examines the legal status of Tunisian migrants in each of these two periods, as well as their access to the labour market, and their day-to-day experiences of racialization. The paper claims that while the legal status of Tunisian migrant workers has substantially improved, and they currently face less explicit discrimination on a daily basis, their economic stability has become increasingly precarious due to the economic crisis hitting multiple productive sectors of the island's economy. Thus, while various Sicilian local governments are celebrating the multiculturalism of the island, its 9th to 11th Century Arab history, and its current connections to Tunisia, many of its well-established Tunisian migrants, particularly those who have acquired Italian citizenship, are looking for possibilities to leave the island, or Italy altogether. While underlining its past and present connections to Tunisia is a way for Sicily to boost its strategic importance within Italy and to capture European Union subsidies, this has not translated into material benefits for the island's Tunisian population.