PurposeThe research aims to explore the relationships between the digital capabilities of micro, small and medium enterprises (MSMEs), their participation in global value chains and their adoption of innovative business models. Additionally, the study investigates how the prior experiences of entrepreneurial failure may influence or moderate these relationships.Design/methodology/approachTo address these research objectives, the study draws upon data obtained from the Flash Eurobarometer 486 survey, a comprehensive dataset that explores the challenges faced by 13,197 European MSMEs as they navigate the complexities of growth, the integration of sustainable business models and the incorporation of digital technologies. To test the proposed hypotheses, the research employs multivariate logistic regression analysis.FindingsDigital capabilities are found to be positively associated with business model innovation, while integration into global value chains is linked to a higher likelihood of implementing new business models. Interestingly, entrepreneurial failure did not significantly influence the relationship between digital capabilities and the adoption of new business models. In contrast, entrepreneurial failure significantly moderated the impact of global value chain inclusion on business model innovation, particularly in MSMEs with a history of failure.Originality/valueThis article provides practical guidance to entrepreneurs and companies interested in enhancing their digital strategies and engagement in global value chains, considering the entrepreneurs' business histories.