Objective: The COVID-19 pandemic made working from home (WFH) the new way of working. This study investigates the impact that family-work conflict, social isolation, distracting environment, job autonomy, and self-leadership have on employees’ productivity, work engagement, and stress experienced when WFH during the pandemic. Methods: This cross-sectional study analyzed data collected through an online questionnaire completed by 209 employees WFH during the pandemic. The assumptions were tested using hierarchical linear regression. Results: Employees’ family-work conflict and social isolation were negatively related, while self-leadership and autonomy were positively related, to WFH productivity and WFH engagement. Family-work conflict and social isolation were negatively related to WFH stress, which was not affected by autonomy and self-leadership. Conclusion: Individual- and work-related aspects both hinder and facilitate WFH during the COVID-19 outbreak.