This chapter chronicles and discusses in a critical way the milestones of over 35 years of Portugal’s European integration, which mirror the growing pains and gains of a transformative journey that has become an integral part the country’s national identity. Taking stock of the international literature, it begins with a tour d’horizon highlighting the major issues and insights regarding Portugal’s experience in the European Union (EU). This historic overview provides the necessary background for shedding particular light upon the Portuguese Presidencies of the EU Council which, taken as a whole, evince the evolutionary Europeanization pathway that has led the country to embrace an ever-integrated political EU. The incremental support shown by Portuguese authorities to task expansion within the realm of security and defence stands out as a paradigmatic example of this. Before its concluding remarks, this chapter offers a view of future avenues and challenges for the field of research.