This article sets out to analyse the Polish-Russian agreement on small border traffic in the context of relations between the European Union and the Russian Federation. The analysis focuses on the role of the Kaliningrad region of the Russian Federation in relations between the EU and Russia and conditions of the Polish-Russian agreement on small border traffic. The methodology employed is based on analysing primary (documents) and secondary (scholarly publications, press articles) sources. The article also addresses the “Kaliningrad question” — one of the most important issues in Russia-EU relations. The analysis shows that the signing of the Polish-Russian agreement on small border traffic should be viewed as a success. Based on the agreement, the inhabitants of borderlands in Poland and Russia (the Kaliningrad region) can cross the border without obtaining an entry visa. For the inhabitants of the borderlands, the agreement brings a range of significant advantages relating to the intensification of social, cultural, touristic, and economic contacts. It is worth noting that the agreement is one of very few examples of EU —Russia cooperation, especially in context of deterioration thereof observed over the last several years.