PurposeThe authors’ aim is to investigate if entrepreneurial orientation (EO) has a role in interpreting an external crisis, such as COVID-19, as an opportunity for investing in digital transformation.Design/methodology/approachThe authors undertook multiple case study research on the digital transformation of seven “Made in Italy” SMEs and proposed a conceptual framework that sees an external stimulus (e.g. the pandemic) as a driver of the digitalisation, filtered by the entrepreneurial orientation of SMEs.FindingsThe authors’ results show how EO deals with the changing environment and helps address the market opportunities related to digitalisation.Research limitations/implicationsThis study contributes to the existing literature on EO and digital transformation of SMEs, creating a new model for forthcoming studies on this topic. In addition, interesting insights are offered on the role of EO to promote the introduction of digital transformation in SMEs operating in the “Made in Italy” sectors.Practical implicationsThis study shows the role of EO as a reactive characteristic during a crisis. Thus, the authors’ suggestion to SMEs is to develop their EO as a part of the strategic orientation. In addition, this work encourages policymakers to invest in the promotion of specific interventions aimed at supporting entrepreneurs in enhancing their capacity to effectively manage digital transformation.Originality/valueIdentifying the most important triggers of digitalisation in times of crisis remains an underexplored area of research. Thus, this study adds value to both digital transformation and entrepreneurial orientation topics.