This chapter examines and compares the legal and policy frameworks shaping civil society organisations (CSOs) in Zimbabwe and South Africa. Through a qualitative, document-based methodology, it explores how CSOs are registered, funded and regulated, assessing the impact of state perceptions, legal environments and democratic commitments on civic space. While both countries constitutionally guarantee freedoms of association and assembly, Zimbabwe’s regulatory regime is notably more restrictive, marked by state suspicion and legal constraints, while South Africa offers a comparatively enabling environment. The study reveals that although CSOs in both contexts face funding and operational challenges, Zimbabwe’s civil society is more vulnerable to political interference and repression. The chapter recommends enhancing legal clarity, promoting state-CSO collaboration and leveraging digital technologies to improve transparency, compliance and public engagement. Findings contribute to broader debates on democratic consolidation, civic participation and the importance of protective legal frameworks for CSO sustainability in Southern Africa.