Remote working during the COVID-19 pandemic comes as an “enforced experiment,” where companies and individuals have turned to work from home to preserve business continuity. Drawing on a theoretical framework that integrates the Theory of Reasoned Action (TRA), Social Capital Theory (SCT), and Technology Acceptance Model (TAM), this research uses a sample of 134 survey responses to assess the factors affecting the acceptance and use of remote work during the COVID-19 pandemic among workers of the insurance industry in Jordan. The results suggest that social trust, perceived usefulness, and perceived ease of use can help elevate employee’s acceptance and use of remote work, whereas social norms have no significant effect. Considering these results, we further discuss implications and recommendations for the insurance sector.