Employing phenomenology as a methodological framework, this study sought to capture and understand, from a first-person point of view, what parents, teachers, and administrators in U.S. high-needs K-12 schools experienced related to online learning during the COVID-19 pandemic. Individual interviews were conducted on a video conferencing platform to collect in-depth information about participants' lived experiences related to online learning necessitated by the pandemic. Findings from the phenomenological data analysis highlight four factors that may need to be taken into consideration when planning, designing, and implementing sustainable online learning in high-needs schools: (a) accessibility: physical and digital; (b) usability: functional use of technology and instructional technology; (c) wellness: physical and mental, social, and emotional; and (d) support: home, school, and peer. These findings contribute to the knowledge base about K-12 online learning by sharing lived experiences and adding to the literature on online education in high-needs schools.