This paper presents a comparative legislative analysis that critically examines the precursors and implementation of online safety legislation on societies in the Global South, using the Caribbean as a focal case study. The online communities that we engage with foster greater human connections, serve as platforms to promote business services, and have become central in public discourse worldwide. Consequently, governance has emerged as a vital approach to maintain healthy digital environments and address the rise of socio-technical harms flowing from online communities. This study employs a two-tiered analytical approach to scrutinize the legislative frameworks established in the Caribbean and to surface variations in policy priorities, approaches to regulation, levels of enforcement, and identify power dynamics that impact the execution of said regulation. The findings of this work shed light on the need for additional work in social computing that delves into the societal ramifications of existing governance structures, rather than solely focusing on efforts to inform and develop new legislation. Through the lens of the Caribbean's case study, this paper provides valuable insights for policymakers and stakeholders in the region seeking to optimize the impact of online safety laws on their societies while highlighting contextually appropriate governance solutions that acknowledge the unique cultural, political, and socioeconomic contexts of the Global South.