While an extensive literature base has focused on online learning, fewer studies have explored the unique implementation challenges in K-12 education. This case study addresses this gap by exploring how an urban, diverse school migrated to a fully online format through the lens of the first- and second-order barriers framework. In terms of first-order barriers, the study highlights the importance of (a) time needed to design and adapt instructional materials, (b) accountability within an online format, and (c) administrator support in the communication process. For second-order barriers, teachers commented on how they perceived online learning to impact important teaching activities (e.g., accountability, timeliness of feedback) and the teacher-student dynamic. Finally, they commented on the challenge to support the socio-emotional component of students and parents in online learning, which is important for school culture and community.