Student disconnectedness remains a serious concern in K-12 online learning--especially in programs where students take most or all of their coursework online. In this research we examined a "shepherding program" designed to encourage a sense of community among teachers and students at an online charter school. Every online teacher served as a "shepherd" for 20 to 25 students and worked to establish close relationships with each student. Data was collected through 5 teacher focus groups, 5 one-on-one teacher interviews, and 10 one-on-one student interviews. A qualitative analysis using Rovai's sense of community framework examined how the shepherding program influenced shepherd-student relationships. The analysis found that the program was successful in establishing a sense of community and students and teachers shared experiences highlighting feelings of spirit, trust, interaction, and learning.