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The crisis triggered by the COVID-19 emergency is changing the competitive landscape by pushing companies to adapt to sudden change. Small and medium-sized enterprises (SMEs) that want to survive must innovate their business. Antifragility represents the capability of a system to absorb shocks and get better, allowing it to overcome a crisis and improve its performance. The use of digital technologies by enterprises is expected to play an important role in building antifragility. The aim of this paper is to study how digital technologies can contribute to the development of antifragility in SMEs. This study analyzed the responses to the COVID-19 pandemic crisis of six small and medium-sized enterprises located in Calabria, South of Italy. All the six enterprises have turned the crisis into a business opportunity developing new products, investing in marketing and communication, or starting new collaborations. The research identifies the factors leveraged by the investigated organizations that enabled this anti fragile behavior. They include slack financial resources, strategic agility, and relations with research institutions. The study highlights the positive impact of digital technologies in developing antifragility. Results were summarized into research propositions to be tested in future confirmatory studies. The findings of the study are useful for researchers interested in antifragility and digital technologies in SMEs. The results are also important for entrepreneurs and managers of SMEs, since they can support their decisions in terms of survival and transformation of their companies., (© The Author(s) 2022.)