This study illuminates the experiences of K-12 educators as they strove to (re)build caring relationships with students during the COVID-19 pandemic. The study was conducted during a graduate course for experienced K-12 teachers in the spring of 2020 at a four-year comprehensive university in the United States. Data was collected from reflective learning journals and asynchronous peer discussions, which captured educators' experiences as they transitioned to remote learning in real-time. Qualitative content analysis was used to identify pertinent themes. Findings suggest that remote learning revealed relationships in need of repair. Educators practiced authentic care and cultivated connectedness by: (1) acting as warm demanders; (2) responding to students' social-emotional needs; and (3) trying to bridge the digital divide. The article concludes with implications for practice and areas for future research as schools, districts, states, and countries consider the "new normal" in K-12 schooling.