Turkey may be entering a “third wave” in the evolution of its modern foreign policy, with continued regional activism played out in a strategic environment that is increasingly insecure and crisis prone. The prevailing mix of self confidence, assertiveness, and coolness toward Western partners may not be sustainable as Ankara once again requires greater reassurance against conflict and chaos on its borders. The return to brinkmanship in the eastern Mediterranean is a further complicating factor, and one that may play a growing role in Turkish-Western dynamics. After a decade of commercial engagement and soft power, hard security issues are returning to center stage. The deepening Kurdistan Workers Party challenge from Northern Iraq, and potentially from Syria, is just one facet of an increasingly troubled security picture across Turkey’s neighborhood.