The advent of social media has transformed the landscape of street gang dynamics. Although existing research has documented gang members’ use of social media—including identity performance, rival taunting, promoting gang culture, and conflict de-escalation—it often lacks a theoretical foundation and process-oriented view of these digital interactions. This study advances a signaling timeline approach to fill this gap. We apply it to a case study of Chicago Latino gangs and qualitative content analysis performed on 2849 posts and thousands more replies and comments web-scraped from a public Facebook page. Our theoretical framework decodes the intricate language of gang communications on social media to uncover the mechanisms behind interpretations and perceptions of gang members’ authenticity and the reasons behind the public nature of what might otherwise be considered clandestine activities. Ultimately this research contributes to understanding the digital negotiation of gang dynamics, highlighting the strategic use of communication in cyberspace.