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This paper investigates the role of a state-run district in supporting organizational learning and improvement among a group of charter management organizations under its jurisdiction. A longitudinal comparative case study was employed in order to explore the experiences of multiple charter management organizations within the school district. The case study approach focused on creating a rich description of the ASD’s process of creating and piloting support systems and the reactions of various CMOs as recipients of these support processes. Preliminary results reveal the portfolio school district design presented significant obstacles for the ASD to facilitate learning. The diversity of providers made it difficult to provide effective feedback and the value of autonomy conflicted with the desire to facilitate learning.