In March 2020, teachers in the K–12 school system were forced to transition from in-person instruction to a variety of virtual teaching models due to the COVID-19 pandemic. This unprecedented change required extensive communication between teachers, students, parents, and administrators. This study explored communication during the March–May 2020 transition period, utilizing Uncertainty Management Theory as an overarching framework to investigate how teacher comfort with online learning, communication overload, administrative clarity, and student–teacher interaction influenced the effectiveness and happiness of teachers. Across these four variables, communication overload was shown to be a strong negative predictor of teacher well-being; student–teacher interaction predicted positive teaching outcomes.