Chapter 2 explores the terms insurgency and terrorism as objectives forms of asymmetric warfare. It explores the concept of insurgency as well the objectives it is focused on, interrogating the traditional and modern terrorist insurgencies and drawing a distinction between counter-insurgency and counter-terrorism. Like insurgency, this chapter deepens the understanding of the concept of terrorism and asserts that the most vulnerable to this malaise are the impoverished and the disconnected in the society. It is also argued here that the modern terrorist insurgent possesses an uncanny ambidexterity in the sense of being not only capable of being an insurgent, but also a terrorist—combining, like the Islamic State (ISIS), the capacity to hold territory with the capacity for organizing dare-devil attacks against civilian populations in both near and far-flung places. This chapter also explores the phenomenon of domestic and/or homegrown terrorists in Western countries—the disgruntled individuals or groups that constitute themselves into lone wolves, having been either radicalized in the internet or influence by those radical Islamists returning from doing jihad in Syria, Iraq, Afghanistan, and other epicenters of terrorist insurgents.