Street art has profoundly transformed artistic expression in public spaces, redefining how it is perceived and experienced. Indeed, it is now exploring new digital dimensions where the boundaries between the real and the virtual are blurring, paving the way for unprecedented creativity. In this context, this research examines how digital technologies are reshaping urban art in an increasingly connected world. The core issue lies in the reinterpretation of street art’s identity in an environment where the distinction between physical and virtual becomes unclear, challenging notions of authenticity and the role of the artwork in this new setting. Moreover, this topic is of crucial importance, as this transformation raises major questions regarding the value of art, public participation, and its cultural and social implications. To address these challenges, the methodology employed combines a qualitative analysis of artworks with a study of social media interactions to capture emerging perceptions and practices. Additionally, the study highlights the challenges and opportunities that digital technologies offer to street art and contemporary artists while encouraging a deeper reflection on the future of art at the intersection of the physical and digital worlds.