Mediterranean ecosystems are biodiversity hotspots, however translating conservation need into implementation has been hindered by their function as working landscapes that integrate both human and natural components. This paper compares oak woodland working landscapes in California and Portugal: can conservation policy be reshaped to conserve Mediterranean oak woodland ecosystems with differing sociopolitical cultural contexts? Each oak woodland's cultural-historical legacy and socioecological system (SES) is described, and how each system can cross-inform improvements to conservation policies is assessed. The SES analysis shows that oak woodlands are managed to maximize revenue from one or more of four resources: forestry, rangeland, agriculture and natural areas. Sustainability of extractable resources may be threatened by replacement rate, land-use history and interdependence with other resources. Non-extractable resources (natural areas) are more volatile and sustainable management is dependent on the voluntary nature of collective-choice rules. Conservation planning and implementation require attention to the characteristic heterogeneity of oak woodlands and to the processes that generate biodiversity, such as fire and regeneration. Conservation plans should aim for the preservation of oak woodland functions (for example multiple use systems) and cultural characteristics (such as keeping people on the land), and governmental and public recognition of the value of preserving these woodlands.