Within the current federal, state, and local contexts of educational reform, teachers must be recognized as central actors in policy work, but rarely do we explicitly consider preparing teachers to become policy actors. Understanding these implications for teacher education, we investigate teacher candidates’ learning of the complexity and dynamism of educational policy through a field-based teacher preparation program. Situated across four unique school contexts in the diverse neighborhoods of Chicago, Illinois, we qualitatively study the cases of eight teacher candidates as they explore policy in practice. We found that candidates developed enduring understandings about policy as complex, situated, and multilayered, as well as the central role of the teacher. This learning was mediated by multiple facets of the field-based module, including readings, panels, and observations. Implications center on the use of field-based teacher education to support policy-related learning and development.