Establishing social connections is crucial for providing exceptional educational experiences, whether in-person or online. However, online teaching presents challenges for principals as it limits their ability to interact with students face-to-face, resulting in less contact time. Additionally, the current COVID-19 pandemic has intensified the administrative demands on school principals, further reducing their available time. This study investigated how school principals develop social relationships with teachers and students online, their feelings about it, their motivation, and how they acquired this knowledge. Using a qualitative, semi-structured, one-on-one interview methodology, the research explored the central question: How and why do school principals develop social relationships with teachers and students online? The findings uncovered that school principals employ various strategies to foster online social bonds with teachers and students. However, while the strategies used with teachers primarily focused on administrative functions and emotional support, those used with students were not intentionally geared towards academic engagement. As such, this research concludes that an opportunity exists for Jamaican school principals to fully harness the power of social relationships to enhance their students' academic performance. Consequently, a recommendation is that principals be offered various training opportunities to become more strategic in leveraging social connections to enrich learning experiences.