Retro art and technology have been on the rise in recent years, the phenomenon is fuelled by the nostalgia of a sense of authenticity that the offline world can no longer satisfy. The integration of technology into human’s social conduct has made it an extension of their beings. Faced with technological progress, people also yearn to regress to the age-old days of their childhood. Nostalgia often comes with romanticization of the past, but it also offers a sense of security and realness that is seemingly lost amid the constant exchange of data in the present time. This lays ground for the rise of faux-vintage photos on social application Instagram. Bracing itself as a modern digital media, Instagram capitalizes on nostalgia for the analog and fetishization of the retro aesthetics of old media. While researchers have noted the link between Instagram and digital nostalgia, these works remained within the theoretical realm. Using a combination of interface criticism and interview, the paper focuses on human and computer interaction to study digital nostalgia and mediated authenticity on Instagram. The findings point out the complexity of Instagram as a social network and a creative tool in the emerging age of pervasive computing, in which the technology increasingly integrates and fades into the background of our everyday lives. The paper’s intention is to develop further understanding of retromodern technology, particularly Instagram, in reconstructing our knowledge of society and everyday social conduct. A better comprehension of our digital culture is crucial to the development of the self and society.