Purpose: The article examines the conditions by which research alliances (RAs) can support district officials in learning how to design and manage more equitable education systems. Special attention is given to the role of theoretically driven research in facilitating learning and the accumulation of expert knowledge. Methods: Results are informed by a 4-year comparative case study involving two established RAs that operated in urban settings. Data included 110 semistructured interviews with RA researchers and staff, district officials, and other stakeholders; observations of social interactions between RA and district staff; and analysis of RA materials, including research reports. Findings: Results suggest that district learning is aided by theoretically driven research that enables practitioners to learn from the clash between their implicit theories and the results surfaced by RA inquiry. Findings further suggest that to support the incremental accumulation of knowledge, RA and district managers need to construct a working field-level theory of improvement that guides inquiry into specific projects and that draws connections among district programs that might otherwise seem unrelated. Implications: Our analysis suggests that for RAs to support districts in learning how to design more equitable systems, they must engage in theoretically driven work that draws connections between the theories of action that inform individual programs and broader theories of improvements. This will require RAs to enhance the theoretical rigor of their work and to enter into more interdependent relationships with districts.