Over the last few years the approaches and the use of the Internet, and the so-called Cyberspace, by terrorist organizations, such as ISIS (Daiesh, in Arabic), dramatically risen up. In today’s world, a fully digitalized, always-on and hyper-connected one, the ICT technology is even more central in the society, which in the meanwhile become a “digital society”. Every relevant sectors of Western economies depend on ICT technology, from Energy Infrastructures to banking and finance, from TLC infrastructure to government administration; over the last three years the yearly reports from the World Economic Forum showed us those dangerous interdependencies, and each one of them risen up those stakes we are facing, as a modern society. Throughout history, terrorist organizations demonstrated the capability to adapt and evolve, in order to further their ideological and political goals; the very recent behavior of organizations such as ISIS showed up their use of the cyberspace in order to deliver propaganda, to demonstrate their power, to raise funds, to show and to share the evidences of their crimes, such as murders, rapes and much more. Nevertheless, it is our opinion that all of this is strongly different from the so-called Cyber Terrorism, while at the same time such a complex terminology – on which most of the States do not have a commonly shared definition and interpretation – is quoted and mentioned all over, and it is increasingly becoming a top five national security priority for Nation States. In addition, actions such as “DDoS attacks” and “Web defacements” should not be considered as “cyber attacks”, and the skills and technology needed today in order to perpetrate these actions are available to any average skilled Internet user. This article aims to draw possible attack scenarios, and identify those potential attacks made possible through IT and ICT technologies, like SCADA and Industrial Automation, while including those ICT standards used in the field of Transportation, Automotive, and more, thanks to the currently available public documentation and relevant case studies.