The hypochondriac feels ill, is reminded they are always ill, and is always told they are never ill because they’re a hypochondriac. They get better, only to read their symptoms as illness again, in a health-illness dialectic that undermines the medical, clinical, or social cure. The social figure of hypochondria embodies the relation between the health-illness of the psyche and the health-illness of the world, as a figure of critique and a coming of age with it. By its very structure, hypochondria is a critical incision in the health-illness and mind-body divides, and it is also a metaphor for a broader modern illness. This essay investigates histories of hypochondriacal symptoms and hypochondria as a historical symptom of the modern condition, that birthed it. Additionally, I include autotheoretical fragments—a historically recurring and amenable form to hypochondria—to better theorize hypochondria’s immanent critique of clinical and medical (un)certainty. Foregrounding the contradiction of a body trying to protect and a body trying to kill, a body lived as an outside threat and a body lived as an inside to protect, the hypochondriac becomes a dialectical diagnostician of what it may mean to seek health in sickness if health is not cure but recurring symptom, struggle, and overcoming.