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The literature positions administrators to be the problem-solving leaders of their schools and districts (Bryk et al., 2015) with the capabilities to explore and solve complex problems in a systematic way (e.g., inquiry cycles), yet many district administrators are not trained to problem solve leading to quick solutions that may not fit the issues at hand. Recently, more attention is being paid to training teachers and administrators to problem solve (Bryk et al., 2015), however this frame has not been applied to special education. Special education administrators (SEAs) problem solve under an unique context, included in, but also separated from the general education context. Additional legal requirements (e.g., individualized education plans) and a separation between special and general education at all levels of the system compounds the tension between the aspirations of special education (i.e., beneficial, individualized education for students with disabilities) and the dysfunctions of such a system in schools (e.g., lack of resources, time). The gulf between aspiration and reality presents many issues that SEAs must problem solve, yet little is understood about how a team of SEAs undertakes problem solving and develops the agency to do so given such fraught circumstances and context.