Reporting terrorism or extreme violence presents a myriad of challenges and dilemmas to media professionals, information managers, and other state actors who are saddled with the responsibilities of objectively, responsibly, and accurately purveying information to ensure effective development communication in society. By the same token, insurgent or terrorist groups spread their inordinate causes, transmit their messages of radicalisation, and garner support, recognition, and legitimacy from the populace through media channels such as handbills, internet, radio, and film. The paradox, therefore, is that in their informational offerings, the media or media professionals have inadvertently become accomplices or victims/endangered species in terror acts. In spite of this, they are duty-bound to report the events regardless of the consequences on the audience(s). Indeed, it has been argued that the sensational reportage and overly dramatization of the activities of extremists groups in the media further propagates terrorist acts. This article examines media reportage of terrorism occasioned by the activities of Boko Haram terrorist sect(s) in Nigeria and the challenges media professionals are confronted with in the line of duty. Mooring itself on the agenda setting and gate-keeping theories of the media, it uses historical-analytic method to interrogate the complex relationship between the media and Boko Haram terrorists as well as the dangers posed to Nigerian media professionals and the collective security of the Nigerian state and even the neighbouring countries.