The war in Syria, which broke out in 2011, turned this Middle Eastern country into a major hotbed of instability across Europe's southern borders. To date, the European Union and its member states have been key donors of humanitarian assistance to Syrian refugees and provided limited non- humanitarian assistance to areas controlled by the opposition. At the same time, the EU has imposed and maintained strict sanctions against the Assad government and denied any support for reconstruction of the Damascus-controlled areas pending the political transition. The growing disagreements among member states and a rapidly changing political landscape on the ground in Syria in favor of the Assad government may hypothetically lead to a transformation of the EU position. However, for the European Union to de- velop a viable approach that reflects new realities will require solving some very complex political dilem- mas. European politicians found themselves in a difficult situation – they do not want to legitimise the Assad government by funding reconstruction, however they cannot ignore the humanitarian situation in the country and their interests in the field of security and migration.