Humanity places a heavy burden on agricultural landscapes, demanding plentiful food, multiple ecosystem functions, and biodiversity conservation. We quantified areas growing ‘brighter’ and ‘darker’ (i.e., better or worse than expected based on extrinsic constraints) for multifunctionality of ecosystem services (ES) over time across a dynamic agricultural landscape. To explore how areas changing in ES multifunctionality, we likewise explored temporal changes in additional features of resilience in social-ecological systems, including: (1) species functional richness and dispersion, (2) agrodiversity, (3) the diversity of farm characteristics and human demographics in the area, and (4) landscape structure and diversity. We found areas increasing in multifunctionality were likewise becoming more biologically and agriculturally diverse, without large losses in overall food production. This suggests the potential for complementarity among goals of food production, multiple ES, and biological and agricultural diversity for agricultural landscapes. While we cannot distinguish whether diversity is the driver, or the consequence, of ES multifunctionality, we can conclude that building diverse, multifunctional agricultural landscapes are an important goal for general system resilience and the future of food security.