In 2021, the authors pivoted their university's Literacy Clinic to online to continue providing literacy services to educators, K-12 students, and families during the dual pandemics of COVID-19 and continuing systemic racism. Alongside of the educators in the Literacy Clinic, they wondered how they would engage students in literacy lessons that would further their agency with literacies in a digital setting while also navigating connectivity, devices and platforms, and the concomitant grief of living in an era of ongoing racial injustices and COVID-19. This paper focuses on a case study of a teacher's journey designing critical literacies online. Data sources include recorded literacy lessons, artifacts of student and teacher learning, and reflective documents. The extended case analysis attended to emergent and fluid meanings made across texts, interactions, and time. Over the course of 12 weeks, one educator's pathways with teaching critical literacies online transformed as she built relationships with her student and his mother, centered inquiry, and scaffolded her student to design a public service announcement. In data-rich vignettes that capture the complexity of critical literacy episodes that cross media spaces, the authors illustrate the transformation of meanings across time, model, and space. This case provides a window into an online critical literacy teaching, an experience that has largely been out of focus.