Ruminant livestock production is arguably the most varied, complex, impactful, and controversial land use sector of our global food system today. Despite calls for improved sustainability across the sector, progress has been limited. To advance effective solutions, there is a need to understand livestock systems and outcomes at regional scales, grounded enough in local conditions to be relevant, yet broad enough to be generalizable for policy or funding interventions. Using a comparative qualitative analysis of ten expert-led case studies from diverse agroecological regions and production systems around the world, we offer an updated approach to categorizing livestock systems, discuss relevant outcomes, and offer insight into the key contextual factors that influence current systems and potential for change. We find that in addition to livestock production system classes, economic (local, regional, and global economics and markets), environmental (biome suitability for ruminant grazing, land condition, precipitation), and social and cultural factors (land tenure, cultural embeddedness of livestock) are important to consider. Our case study analysis also shows that livestock management is typically motivated by at least five outcomes, with priority outcomes shifting from region to region, highlighting that livestock plays different roles, with different implications, in different places. We conclude that use of a context-based lens considering multiple outcomes and perspectives will likely improve the pace of progress toward environmental and social sustainability of livestock production.