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Attrition rates among school leaders have risen in recent years, and scholars cite a lack of meaningful connections and responsive professional learning as leading reasons why they are leaving the field. School leaders are called to navigate unfamiliar and complex challenges, often working in isolation with limited opportunities for collaboration and professional growth. Social media forums, like Twitter, have potential to support a Community of Practice to facilitate learning around school leadership; however, there is a lack of scholarship exploring how school leaders use social media to support their needs. This mixed-methods study used sentiment and content analysis along with a phronetic iterative approach to explore how school leaders use Twitter to connect with others in the field. The umbrella categories of efficacy, agency, and resiliency emerged from the analysis, offering a glimpse into potential connections made through social media. The findings of this exploratory study suggest that principals are seeking connection, encouragement, and professional learning, yet further development in this area could help inform more formal practices to fill the gap in access to informal professional learning.