This study investigates the antifragility of organizations, especially in strategic sectors highly exposed to disruptive events. Based on a qualitative approach with case studies in the wine and textile sectors in Portugal, the findings indicate that financial and market strength, as resilience capabilities, operate interdependently and are reinforced by digital maturity and supply chain integration. Companies with financial robustness and strong market intelligence tend to be more agile in strategically investing and reallocating resources during crises. The research adopts an expanded definition of antifragility, which incorporates resilience, innovation, and strategic reconfiguration in the face of disruptions. It concludes that organizational antifragility results from the articulation of financial resources, market intelligence, and digital collaboration, offering a sustainable competitive advantage in the face of uncertainty. The study contributes to theoretical debates and provides practical recommendations for managers and policymakers.