This paper analyzes the breaking of diplomatic relations (and variations thereon) as a strategic resource, focusing on security issues in the Middle East. We base our analysis on three key instances in the history of Franco-Syrian relations. The 2004–2005 diplomatic rupture, presented as irreversible, offers the opportunity to evaluate the centrality of Lebanon’s role in Franco-Syrian ties as conceived by Jacques Chirac. The 2007–2008 rupture, which appears to have been more negotiable, hinged on the role France sought to play in regional issues, especially with respect to peace between Syria and Israel. Finally, the 2011 breakdown of diplomatic relations can be interpreted as a gamble on finding an alternative to the Syrian regime. These breaks were rooted in complex regional variables that either caused them or were influenced by them.