Contemporary societies have succeeded—unequivocally—in minimizing many forms of physical hardship, risk, and scarcity. This success, however, brings with it a paradoxical phenomenon: a tendency for subjects formed within highly comfortable environments to exhibit increased psychological sensitivity, lowered tolerance for friction, and diminished capacities for sustained agency. I call this phenomenon “privileged fragility” and theorize it as the comfort–fragility paradox: beyond a certain threshold of environmental amelioration, gains in comfort correlate (structurally and causally) with losses in psychological robustness. This paper advances a conceptual and philosophical analysis of privileged fragility, situating it in dialogue with Nietzschean critiques of modern complacency, Adorno and Horkheimer’s diagnosis of the culture of administered life, Foucault’s account of biopolitics and self-regulation, and contemporary discussions of burnout, therapeutic culture, and “coddling.” I develop three interlocking arguments—phenomenological, structural, and normative—showing how comfort reshapes attention, habit, and agency; how institutional and cultural technologies amplify sensitivity; and why these changes matter normatively for autonomy, political agency, and the good life. I conclude by sketching avenues for resisting pathological comfort: cultivating practices that reintroduce calibrated friction, reconceiving social aims to include resilience as a civic good, and revalorizing virtues of endurance and experimental exposure within ethical education. Keywords: comfort, fragility, modernity, subjectivity, resilience, biopolitics, therapeutic culture