Drawing on the work–home resources (W-HR) model and conservation of resources (COR) theory, in this study we explore how flexibility i-deals relate to employees’ work performance through their family performance. In line with the W-HR model, we introduce two contextual conditions to explain when our proposed associations may unfold. One is a facilitator: perceived organizational support (POS); and the other is a stressor: perceived hindering work demands. The results of a matched sample of employees and their supervisors working in two companies in El Salvador support our hypotheses. Our findings show that the benefits of flexibility i-deals to the work domain (i.e., work performance) extend only through the family domain (i.e., family performance). Our findings also emphasize that flexibility i-deals do not unfold in a dyadic vacuum: For employee who perceive organizational support to be higher, the association between flexibility i-deals and family performance is stronger, while for employees who perceive hindering work demands to be lower, the association between family performance and employee work performance is also stronger. We contribute to i-deals research by a) exploring a relevant mechanism through which flexibility i-deals influence work performance; b) integrating the role of social context to emphasize the social aspects of i-deals; and c) enriching the i-deals literature by introducing a resource perspective.