The transition from face-to-face education to a primarily teleworking atmosphere following the Spring 2020 onset of COVID-19 left many faculty members floundering, struggling to effectively utilize online learning and communication platforms; to feel connected; and to continue accessing collaboration and professional development opportunities. This qualitative phenomenology study is one of the first in-depth qualitative reviews to explore faculty’s perceptions toward connectedness since teleworking as a result of the COVID-19 pandemic. This study was conducted during the Spring and Summer semesters of 2020, when the initial spread of COVID-19 occurred, forcing professionals and students alike to stay home to learn and work. The participants in this study included 11 full-time faculty from two universities in the United States who taught primarily face-to-face classes prior to COVID-19 and began teleworking as a result of the pandemic. The findings suggested faculty faced a slew of challenges related to communication, collaboration, and a sense of community while teleworking as a result of COVID-19, including ineffective communication, technology and access challenges, a lack of time and training, and feelings of disconnect. Participants also outlined strategies they believed to be effective to support connectedness while teleworking, such as video conferencing, regular communication, and enhanced collaboration opportunities. Given the volatile nature of COVID-19 and its implications for higher education institutions, it is highly likely that issues relating to connectedness while teleworking will remain relevant for the foreseeable future. Faculty and postsecondary administrators may use the findings from this study to guide discussions about whether their efforts to enhance overall perceptions of connectedness and faculty satisfaction have been successful, or whether efforts need to be revisited, revised, or enhanced.