During the COVID-19 pandemic, telework emerged as a pivotal strategy to mitigate the spread of the virus. However, telework’s feasibility was contingent on job roles. This gave rise to two distinct groups: teleworkers and on-site workers. However, the impacts of social support and well-being extended to both groups. This study investigated the link between organisational and supervisory family support and subjective well-being, examining work engagement as a mediator. Conducted in Portugal, this cross-sectional study surveyed 515 individuals via web-based questionnaires. Data were analysed using descriptive statistics, correlation analysis, confirmatory factor analysis, and multiple-group analysis. The findings revealed a positive correlation between perceived organisational family support (POFS) and work engagement for both groups. Additionally, perceived supervisory family support (PSFS) positively correlated with work engagement for telecommuters but not on-site workers. Furthermore, work engagement was positively associated with subjective well-being for both groups. Moreover, work engagement mediated the relationship between POFS and subjective well-being. This study enriches the literature by analysing POFS, PSFS, work engagement, and subjective well-being dynamics among teleworkers and on-site employees.