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The present chapter aims to assess how digital transformation impacts current trends in city branding, to analyze the role of digital communication in the branding of selected cities, and to compare the level of exploitation of digital communication for city branding between European and Slovak cities. We conducted empirical research in several phases, and the overall sample consists of 155 cities in Europe and Slovakia. The results of our research showed that European and Slovak cities use to some extent all the investigated tools of digital marketing communication in city branding with a dominant position of social media, both in terms of exploitation and importance for city branding in European and Slovak cities. European cities score significantly better than Slovak cities in all elements of the City Brand Hexagon, as well as in the overall city brand index. Therefore, city branding strategies in the best European cities can serve as a good practice example or inspiration for Slovak cities. Cities with lower rankings and scores on city branding should focus on strengthening their city branding or strengthening their digital communication. The possible trajectory is also the concerted strategy for the branding of the city and its digital communication.