This chapter focuses on how Italy’s position as a key port of entry for migrants reaching Europe has influenced shifts in trends and policy, including external border governance, as well as asylum protocols and reception and detention policies. We situate Italy in the post-1985 Schengen context, as Italy has negotiated its position at the EU’s southern borders, in relation to “Fortress Europe.” These years mark Italy’s shift from a country of emigration to an immigrant destination, and post-1989 policy in the country can be understood as an ongoing attempt to respond to and regulate this change.