Over the past twenty-five years, Cartagena has played an important role in facilitating Colombia's transition from drug-and-arms isolationism to Summit of the Americas host and New World financial hub. Cartagena maintained its reputation for beauty and tranquility throughout the most destabilizing decades of an internal armed conflict that plagued the interior of the country from the late 1980s through the early 2000s, yet since the official end of the conflict, Cartagena has experienced a steady increase in extrajudicial violence and cartel-related investment, influence, and insecurity. My dissertation interrogates the concepts of insecurity, pro-social coping, and subjective well-being (SWB) in contemporary Cartagena, Colombia. I provide an anthropological response to what social psychologists have called "the Colombia-Japan Paradox," or the question of why Colombians are unique in reporting extremely high subjective well-being despite their acknowledgement of extremely high insecurity in their immediate environment (Diener 2005; Willis-Herrera et al. 2009). In my interviews with 120 participants, I found it is not well-being and security that are considered mutually constitutive categories in Cartagena, but well-being and health, or the belief that if a person cannot maintain a sense of well-being despite insecurity, then the individual is likely to experience a major health crisis in the form of a chronic illness or a psychotic break. In Cartagena, well-being despite insecurity is maintained through a number of complex collective coping strategies, the majority of which focus on pro-social engagement with others in the community. My research provides further insight into how populations collectively adapt to new forms of violence while rejecting previous "culture of terror" paradigms (Taussig 2005) that misrepresent and stigmatize Colombians as a chronically anxious and socially withdrawn population