This dissertation is about one of the most despised activities that health and human service professionals are obligated to do: maintaining documentary standards. Documentary standards are the written rules that specify how a person writes, types, clicks, fixes, stores, arranges, and reports on activities and objects. Not surprisingly, people’s complaints about documentary standards are legion. They routinely lambast clicking boxes in the putative name of effectiveness and focusing on paper rather than on people as pointless, time-consuming, and counterproductive to the goals at hand. Drawing from 16-months of ethnographic fieldwork at a large, federally-funded healthcare organization in Midwestern United States, I ask, what accounts for professionals’ sustained determination to maintain standards, even those they are vexed by? To answer this question, this dissertation will offer an account based on ambivalence. The account rests on two claims. First, standards are plastic. Their meanings, practices, and consequences change depending on the situation they are in. A standard that seems trivial in one context might become immensely consequential in another. After all, even the smallest slip from standards—a document incorrectly filled-in, not filled in at all, misplaced, or lost in transit—can really make a difference not only to an organization’s receipt of money and possibility of malpractice claims, but also to the life and death of patients. Second, humans are ambivalent. Humans are capable of holding contradictory views towards the same object or task, which enables them to view the once seemingly trivial standard as immensely consequential, even embracing some standards as a cause. Taken together, my argument is this: a standard’s potential to shift from the realm of triviality to the realm of consequentiality, alongside humans’ capacity to mobilize ambivalence, is what commits professionals to maintaining standards. To make this argument, I will recount a series of adventures with standards. We will join healthcare professionals as they audit electronic medical records (chapter 1), devise schemes to get frontline workers to click boxes (chapter 2), conduct a risk audit of the clinical environment (chapter 3), and engage in activities to contort cervical cancer screening documentation into standardized form (chapter four). I will draw attention to the dizzying array of work—all the frustrations and seeming futility as well as the passion, pleasure, and even a sense of personal duty—involved in maintaining standards, and articulate the effects of that work on interpersonal relations, professional power, and social and organizational reproduction. Along the way, I will pay attention to ambivalence—how it is provoked, mobilized, and to what effects—to show how professionals use ambivalence to help them come to terms with the seeming absurdity of their work. In so doing, this dissertation aims to help professionals who work in health and human service organizations better understand and productively do something about their own ambivalence in settings that foster ambivalence.