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Some districts have begun to give their principals opportunities to collaborate with peers. Theoretically, such opportunities could provide valuable learning opportunities and foster professional connections. However, well-intentioned efforts to promote collaboration often fail. This study seeks to understand one urban district’s attempt to encourage principal collaboration through an initiative called affinity groups. Affinity groups provided principals with autonomy and freedom to pursue their own learning. This study investigates the positive and negative outcomes of providing such freedom to three collaborating groups of principals. Some principals capitalized on their freedom by investigating controversial but important topics and engaging in authentic conversations. Other principals experienced disorganization, disengagement, and internal conflict. Results have implications for districts considering promoting principal collaboration.