Although the merits of in person learning outweigh those of virtual learning for elementary students, online learning is often implemented in response to rising cases of COVID-19. As such, the significant number of barriers to remote learning must be addressed in order to promote effective and health conscious learning for students during the pandemic. Students have been facing challenges with self-regulation, work management and lack of socio-emotional connections while teachers have been facing obstacles related to effectively using technology to deliver content and engage students. Parents have struggled to understand and fulfill their role supporting their children within the online school environment. Considering the perspectives presented in the literature, efforts should be made to promote connectedness and support for families during this difficult time. A resource toolkit is suggested for caregivers of children enrolled in online school to implement strategies at home to assist their children in their education.