Significant advances in teleworking have received a lot of attention, particularly in the post-COVID-19 age. This research aims to shed light on the teleworking landscape in Spain, providing a comprehensive analysis from 2017 to 2020. Using data from the Spanish Labor Force Survey (SLFS), our study investigates the likelihood of teleworking, with a strong emphasis on individual characteristics. Our findings are varied. Notably, we discover a potential short-term increase in teleworking between 2017 and 2019, a phenomenon that assumes significant significance in the context of the global pandemic in 2020. We use probabilistic regressions that control for a variety of sociodemographic factors to identify the determinants of telework. Surprisingly, we discover that family composition, including the presence of children, has only a minor impact on the likelihood of teleworking. Furthermore, our research indicates a significant shift in gender dynamics, with women showing an increased proclivity to telework in the critical year 2020. Occupation emerges as a key factor, with highly skilled, educated workers in telework-friendly roles experiencing a significant increase in teleworking likelihood in 2020. Gender differences in teleworking, on the other hand, persist, implying more complex occupational dynamics such as contract type, sectoral differences, and work commitment. Our research differentiates three occupational categories: jobs that are naturally suited to teleworking, jobs that require physical presence, and jobs with untapped teleworking potential. We contribute valuable insights to the ongoing debate on remote work in a rapidly changing world by delving into the nuances of telework adoption. While our study offers valuable insights, it’s important to consider these limitations when interpreting findings and implications for telework legislation and practices. Telecommuting, like any labor market regulation, requires thorough scrutiny due to its dual nature.