Libya has been a central focus of European migration management across the Mediterranean for the past two-three decades, becoming particularly salient in 2015–2016. Italy has been involved in a gradual accumulation of agreements with Libya and in recent years also involving the EU. Italy’s prior and contested colonial history in Libya has shaped the close economic ties between the two countries following Libyan independence. Both the colonial history and economic collaboration in turn play an important part in the agreements on migration, something that has hitherto been under-researched and inadequately understood. This chapter presents the history of these agreements, in order to better understand what it means for the EU’s present involvement in them. We also show how European and Italian migration management together with Libya operate in a landscape of treaties and agreements that run the risk of obstructing and obfuscating the rule of law and humanitarian treatment, ideals the EU purports to uphold also in their treatment of would-be migrants crossing the Mediterranean. By taking a historical approach and describing these developments over time, we contribute to better enlighten today’s relationship between the EU and Italy on the one hand and Libya on the other.