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A common criticism of field researchers is that they miss the sociological forest of structures and institutions for the trees of interaction, or alternatively impose macro-theory without justification. How can ethnographers responsibly make micro-macro claims, engage history, and contribute to broader sociological theory? Dilemma Based Ethnography starts with our research subjects’ conundrums and attempted problem-solving solutions, and then utilizes a set of counterfactual and case comparative procedures to tease out multi-level connections. The paper draws on an ethnography of psychiatric treatment in Los Angeles and a practical dilemma: how can authorities manage serious mental illness when patients have rights to refuse care? I note a series of strange "solutions", like social workers placing psychotic patients in subsidized housing with few rules, or police tolerating homeless encampments, that lead to community outrage and new problems. To move "up" and "out" from this situation, I begin by counterfactualizing (asking “why is this a dilemma?”) to generate a series of logical alternatives and comparisons (e.g., authoritarian regimes which eschew patient rights) that clarify the importance of liberalism. I historicize (“where did this dilemma come from”) and trace it to specific policy and cultural conjunctures of the 1980s. This leads me to how structural conditions—in this case civil libertarianism and fiscal austerity—combine to shape organizational dilemmas and interactional problem situations on the ground. I can then theorize across cases by identifying similar structure-organization-dilemma packages, such as changes to drug policy or the school-to-prison pipeline in the post-2020 move against mass incarceration. Put differently, my approach combines institutional ethnography’s interest in contradiction and pragmatism’s action sequences with the logics and procedures of comparative history. This offers a route toward using ethnographic cases to develop sociology writ large, while staying true to the richness and methodological comparative advantage of field research.