This study analyzes the operational features of the work integration social enterprises (WISEs) in Taiwan and Hong Kong from the five dimensions including organizational structure, employment and poverty reduction, the successful factors of management, the challenges and obstacles encountered by operation, as well as the relationships between WISEs and government and business. By utilizing the multiple methods of in-depth interview, literature review, and field observation etc, this study attempts to achieve the goal of the further understanding of the WISE's operational efficiency and effectiveness in the two regions The findings from this study highlight that , both in Taiwan and Hong Kong, voluntary and social organizations are the main legal forms of WISEs, the operational size of WISEs keeps small to medium, and lastly, this kind of social enterprise continues to provide employment opportunities for disadvantaged groups to address those problems resulted from economic and social dysfunctions.