During COVID-19, many schools in the United States restrict parent visits and parent-teacher face-to-face meetings. Consequently, teachers and parents rely on digital technologies to communicate and build partnerships. Yet, little is known about their perceived experiences with digital communication. To contribute knowledge to this area, this study investigated the perceptions of the classroom teacher and parents of preschool children concerning their experiences of communicating with each other via digital technologies during COVID-19. The participants consisted of one teacher and three mothers of 3-year-olds in the same classroom of a private childcare center serving preschool children from mostly middle-class backgrounds in a northeastern state of the United States. The teacher and parents were interviewed individually and virtually via Zoom for 30–60 min (M = 45 min). A thematic analysis uncovered four salient themes: (1) modes of digital communication between the teacher and parents, (2) the nature of digital communication, (3) limitations of digital communication, and (4) digital communication via ClassDojo. The ClassDojo theme further revealed three subthemes: (1) ClassDojo for promoting proactive parent involvement, (2) ClassDojo for building teacher-parent partnerships, and (3) the use of limited functions of ClassDojo. The data were triangulated by analyzing teacher-parent communication artifacts on ClassDojo, which confirmed the findings related to the use of this digital platform.