The EU's relations with countries in the Southern Mediterranean have a long history as the region is of great strategic importance for the Union and its member states. The High Representatives of the Union for Foreign Affairs and Security Policy have been highly involved in shaping these relations, and this role has been officially strengthened with institutional changes brought about with the Lisbon Treaty. This article analyses the role of the HR/VPs in shaping the EU's foreign and security policy towards the region with an analytical focus on discursive practice. Drawing on insights from practice theory in IR and EU studies, the analysis traces continuity and change in how the Southern Mediterranean is described in the drafting of key strategic documents. The main finding is that EU foreign and security policy towards the Southern Mediterranean shows a high degree of continuity despite several crises and institutional changes, although the discursive practices have evolved. The article ends by highlighting a conundrum that the EU can be said to implicitly acknowledge: if authoritarian states in the Southern Mediterranean are inherently unstable, yet stable enough to quench the democratic aspirations of their people, then what should be the basis for EU actions?