This paper presents a study in capturing the impacts of the mandatory pandemic-induced telework practice on workers’ perceptions of the benefits, challenges, and difficulties associated with telecommuting and how those might influence their preference for telework in the future. Data was collected through an online survey conducted in South Florida in May 2020. Survey data showed that telework indices (either measured through actual behavior or stated preference) before, during, and after the pandemic were heterogeneous across socio-economic, demographic, and attitudinal segments. Before the outbreak, males, full-time students, those with PhD degrees, and high-income people showed higher percentages of involvement in jobs with a telework option. They also had higher pro-technology, pro-online education, workaholic, and pro-telework attitudes. During the pandemic, professional/managerial/technical jobs as well as jobs with lower physical-proximity measures showed the highest telework frequency. In view of future telework preferences, our analysis showed that those who were more pro-telework, pro-technology, and showed less dislike of telework dislike preferred higher telework frequency. A structural equation model was developed to assess the impacts of different predictors on telework behavior before the pandemic and preferences after the pandemic. While telework frequency before the pandemic was highly affected by the pro-telework attitude, the after-pandemic preferences were influenced by several other attitudes such as dislike telework, enjoy interaction, workaholic, as well as productivity factors. This might confirm the assumption that the mandatory practice through the pandemic has provided employees more experiences with work-from-home arrangements, which could reshape decisions and expectations around telework adoption in the future.