This chapter focuses on the changing nature of street life and street culture because of the rise of technology. The central importance of the physical streets as a space has been an integral element of the landmark studies of street and gang cultures, dating back to the scholarly attention for the spatial configuration of the urban city by the Chicago School. In addition to functioning as a staging area for violent confrontations, scholars have identified a variety of instrumental criminal activities on the streets, ranging from ‘amateur and playful’ to professional, high-end and high-value criminal transactions. The internet, and social media in particular, is increasingly used by gangs and gang members to showcase and promote gang culture. However, research in the burgeoning field of cybercrime indicates that not all street-oriented individuals or gang members need highly advanced technological skills to engage in these cybercrimes.