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Principals face heavy workloads, varied pressures, and have limited opportunities for collaboration. Social media platforms, like Twitter, provide a space for school leaders to connect personally and professionally, but there are considerations to connecting within an open forum. This study investigates how school leaders are using Twitter to create a Community of Practice while also examining stakeholders who are placing themselves within the CoP. Using targeted hashtags, the primary dataset of 28,165 tweets was preprocessed for increased efficacy and analyses were conducted through a multi-layered approach of machine learning sentiment analysis, secondary qualitative analysis, axial coding and collaborative coding. The implications of the findings may provide guidance and considerations for school leaders in the use of social media.