This study examines the role of civil society in responding to democratic challenges in Indonesia and the Philippines within the ASEAN context during 2019–2026. While prior research has addressed civil society, digital activism, populism, and institutional safeguards separately, few studies integrate these dimensions in a comparative framework. This study aims to analyze how civil society strategies, state responses, digital activism, electoral mechanisms, and legal safeguards interact to support democratic sustainability under increasing populist and institutional pressures. Using a qualitative comparative approach with a case study design, the study analyzes secondary data from journal articles, policy documents, democracy reports, digital archives, and credible media sources, examined through thematic analysis and cross-case comparison. The findings suggest that in Indonesia, civil society employs hybrid digital activism, community-based advocacy, and judicial mechanisms to navigate oligarchic influence, fragmented electoral law, and digital polarization. In the Philippines, civil society faces stronger populist repression, state-led constraints, and shrinking civic space, yet maintains adaptive resilience through strategic litigation, human rights advocacy, international networks, and local mobilization. These findings highlight the critical role of adaptive civil society and institutional safeguards in sustaining democratic processes, while emphasizing that democratic resilience cannot be inferred solely from formal electoral institutions. This study contributes conceptually by framing civil society as a socio-political infrastructure that mediates between citizens and institutions, extending theoretical understanding of how hybrid activism and civic strategies support democratic sustainability in ASEAN. The study is limited to Indonesia and the Philippines during 2019–2026, and results should be interpreted cautiously when considering broader generalizations.