This editorial introduces the Special Issue on the darker dimensions of digital entrepreneurship. While digitalisation has been widely associated with opportunity, empowerment, and innovation, the contributions in this issue demonstrate how it simultaneously produces constraints, asymmetries, and unintended consequences that complicate these optimistic narratives. Taken together, the five articles explore paradoxes within digital business models, consider the social and economic dimensions of platform-based work, and reflect on the evolving futures shaped by emerging technologies in entrepreneurial ecosystems. This highlights the need for more developed theoretical perspectives capable of capturing both the opportunities and the constraints inherent in digital entrepreneurship. Although the extent to which these darker dimensions are explicitly addressed varies across the articles, each offers important insights into the frictions and contradictions that characterise digitally mediated entrepreneurial activity. By bringing these perspectives into dialogue, this Special Issue advances a more critical understanding of digital entrepreneurship, moving beyond celebratory accounts to engage with its sociotechnical complexities. The editorial situates the Special Issue within the broader literature, introduces the individual contributions and outlines a future research agenda.