The outbreak of the Syrian uprising was viewed by many in Turkey as a rare opportunity for the manifestation of Turkish regional leadership. The rising prestige of Turkey in the Middle East was expected to help the country lead the region towards democratization. The European Union also considered these developments a key moment for the promotion of its own foreign policy agenda in the Mediterranean. The collapse of authoritarian regimes was hoped to pave the path for democratic consolidation and better human rights protection. Yet developments followed an unexpected path. The Assad regime proved more resilient than expected, and secularist, pro-Western and moderate Islamist opposition forces were soon overtaken by two leading jihadist forces, the Al Nusra Front and ISIS. In particular, the rapid growth of ISIS influence, its spread into Iraq and the conquest of the country’s third biggest city Mosul and large parts of Iraqi territory posed a major predicament for Turkey and the international community. While the international community was shocked by the brutality and depravedness of the ISIS regime as well as jihadist attacks in European cities, Turkish authorities appeared less concerned: This raised international concerns about Turkish sectarian tendencies, its willingness to collaborate in the struggle against jihadists as well as its own strategic goals in Syria. Turkey’s determination to bring an immediate end to the Assad regime, apparent preference of jihadists to Kurdish opposition groups in Syria and acquiescence regarding the redrawing of the Middle East map attempted by ISIS appeared to overcome concerns about the regional and global repercussions of a jihadist takeover in Syria distanced Turkey from the international community. This paper aims to discuss the challenges that the rise of ISIS has posed for the conceptual foundations of EU and Turkish foreign policy in the Middle East, as well as the motives behind EU and Turkey’s positions on this issue. It will be argued that pragmatist views have pushed Turkey from its original indulgent position on the rise of jihadism in its immediate vicinity to a more circumspect one, which remains however far from mainstream views among the European Union, other Western allies and most Middle Eastern states. This paper will be based on foreign policy analysis literature and literature on EU, Turkish, Syrian and Middle Eastern politics, as well primary sources from Turkish, German and English-language press.