This article reconsiders the depiction of boredom in Anton Chekhov’s plays. Against the notion that boredom is a form of ambient gloom that contributes to his “theatre of mood” (in Vsevolod Meyerhold’s enduring phase), I suggest that boredom is, for Chekhov, a disease with a narrowly patterned pathology, which he mobilizes as a dramatic technique. Chekhov’s formulation of “pathology plays” allowed him to make implicit recommendations to the intelligentsia about how to remedy their stultification, even as he avoided outright moral or political prescriptivism. His audiences are made to feel alongside his characters, not only through straightforward identification with their diagnoses, but also through a minimalist aesthetics that causes boredom to redouble itself in seeping from the stage into the auditorium. By focusing on the widespread understanding, in turn-of-the-century Russia, of boredom as a disease, I show how Chekhov was able to maintain the objectivity of a physician while putting the pain of boredom into a narrative, dialogic form.