This article documents, contextualizes, and theorizes the significance of technological divides and inequalities of access, along with diverse accommodations, adaptations, resistances, and alternatives to health and communications technologies that have unfolded in two South American countries during the COVID-19 emergency: Ecuador and Argentina. Based on a shared qualitative interview methodology that focused on issues of social inequality and digital divides, perceptions of and experiences with public health systems, and levels of trust relative to governmental, media, and other sources of information about the pandemic, our emergent comparative analysis demonstrates both shared and divergent patterns. While interview data from both countries emphasize deepening crises of poverty and inequality that reverberate in differential access and usage of communications technologies, there are distinct patterns with regard to confidence in medical systems and public health information. In Argentina, citizens may question or doubt official sources of information and public health systems but, on the whole, tend to maintain higher levels of cautious trust, while in Ecuador, an erosion of trust, along with higher levels of cultural diversity, drives an adaptive response towards systems and practices of medical pluralism, particularly in indigenous and rural contexts. Explanations for these differences may lie in the distinct forms the project of colonial modernity, and resistance or adherence to it, has taken in each country.