This study investigates the unique challenges and success factors of healthcare startups operating at the intersection of digital innovation and healthcare. By employing a mixed-methods approach combining quantitative fuzzy-set qualitative comparative analysis (fsQCA) with qualitative insights from interviews and case studies, we aim to uncover the complex configurations of contextual internal and external factors influencing the success or failure of digital healthcare startups. The research responds to the call for industry-specific perspectives that account for the distinctive challenges and opportunities presented by the rapid advancement of digital technologies in the heavily regulated healthcare sector. The findings are expected to contribute to Information Systems theories on digital entrepreneurship, provide actionable insights for stakeholders in the digital health domain, and ultimately foster the development of sustainable and impactful digital health ventures that drive innovation and improve patient outcomes.