How was the Digital Caliphate organized on Telegram? Was there any leadership within this community? Who were the main actors part of it? How did the trust-building process work amongts strangers but close to the same extremist ideology? Furthermore, what were the expressive, communicative and symbolic features of the online jihadist culture?The "Think Terrorist" approach, a process that immerses the researcher within the extremist perspective, is not limited to being an academic exercise but becomes an analysis tool that helps identify future threats. Interpreting the jihadist ecosystems and the role of technology increases our understanding and provides new insights for future prevention strategies. That is the challenge that poses academics and law enforcement agencies as increasingly converging actors in fighting against terrorism.