This chapter presents a case study on the evolving trajectory of Thailand’s social entrepreneurship ecosystems, revealing a novel bifurcation into two parallel yet interrelated systems: one traditional and certification-based, and the other emerging, technology-driven, and informal. Drawing on qualitative data from key ecosystem actors—including government officials, incubators, academics, and digital social entrepreneurs—the study identifies how investor requirements and institutional misalignments have prompted emerging digital social enterprises to selectively disengage from formal structures. While traditional literature conceptualizes ecosystem evolution as a gradual and integrative process marked by mutual adjustment, the Thailand social entrepreneurship ecosystems case demonstrates a sharp divergence and institutional avoidance. The findings highlight the need for adaptive ecosystem governance and updated certification frameworks that better accommodate diverse entrepreneurial logics. This study contributes to ecosystem theory by introducing bifurcation as an alternative evolutionary pathway and emphasizing the role of ecosystem architects in navigating this complexity.