Digital social innovation (DSI)—the novel use of digital technology to address societal challenges—plays a critical role in our collective pursuit of sustainable development. In this practitioner paper, we present an in‐depth DSI case study where the grassroots communities in a remote county leveraged e‐commerce to leapfrog out of poverty, becoming successful entrepreneurs with online businesses that thrive on a global scale. Based on this case study, we first discuss three leapfrogging opportunities afforded by e‐commerce, which were successfully embraced by the grassroots communities to begin the transformative journey. We then reveal three obstacles that emerged during the technology leapfrogging process, which have challenged the sustainability of the grassroots DSI endeavour. Lastly, we discuss three top‐down interventions that have been instrumental in overcoming the bottleneck of grassroots leapfrogging development and subsequently nurture a self‐sustaining, resilient community. Overall, by discussing some of the common barriers to the growth and sustainability of DSI, and how they have been addressed, this article offers insights and recommendations for policymakers, public and private sector practitioners, and communities in underdeveloped regions to navigate both the potentials and pitfalls of technology leapfrogging, and ultimately build a pathway towards resilience and sustainability.