Extant scholarship increasingly attends to the mixed—and paradoxical—incorporation of information and communication technologies in social lives. Building on existing research, this study further explicates how digitally mediated (dis)empowerment paradoxes stem from the interactions among unevenly transformed structural affordances and constraints in the political, market, socio-cultural, and technological realms under digitalized contexts. Drawing on ethnographic data on women-led digital group-buying during the coronavirus disease 2019 lockdown in Shanghai, China, this study illustrates that the pandemic-inaugurated digitalization paradoxically transformed existing technological constraints into digital resources and techno-skills for women to lead digital group-buying and empower them socio-technologically. Yet these empowerments paradoxically turned into new gender inequalities, as entrenched state and market inequalities compelled female organizers to meet added or dueling burdens. This study, therefore, contributes to understanding the re/configuration and varied interaction patterns of different facets of structural affordances and constraints that condition digitally mediated (dis)empowerment paradoxes under digitalized contexts.