The COVID-19 pandemic brought unprecedented changes in global work dynamics including mandating telework for most of the U.S. federal workforce to protect employees from health and safety hazards of the communicable virus. Although not ubiquitous, many federal employees had experience with these arrangements because they voluntarily chose telework prior to the pandemic through provisions in the Telework Enhancement Act of 2010. Using the 2020 Federal Employee Viewpoint Survey (FEVS), which focuses on telework perceptions and experiences, this study explores the effect of the involuntary telework mandate on employees’ attitudes toward telework after several months through a prospect theory framework. Findings demonstrate that several factors including previous telework experience and experiential learning may influence employees’ preference for and voluntary selection into telework moving forward. These dynamics suggest an endowment effect for telework among employees who gained telework experience before and during the pandemic. In addition, employees may choose telework as an alternative work arrangement when they are not satisfied with their organizations or jobs but want to maintain employment. These findings suggest that agencies should continue to offer robust telework opportunities to satisfy and retain employees.