Building on the entrepreneurial orientation (EO)-as-experimentation perspective, we examine how configurations of the EO dimensions (innovativeness, risk-taking, and proactiveness) might lead to high and low firm performance, and how the configurations differ under different firm contexts. We adopted a configurational approach and applied fuzzy-set qualitative comparative analysis (fsQCA) to a sample of 110 UK small and medium-sized enterprises. Our findings show that three (four) configurations can result in high (low)-firm performance, demonstrating that the EO dimensions can contribute to as well as hinder firm performance. Moreover, the configurations leading to the same outcome are distinct between high-tech and low-tech firms, indicating that the impacts of the EO dimensions on firm performance depend on the firm context. Our findings offer useful insights for managers on how to configure the portfolio of firms’ entrepreneurial activities to achieve superior performance.