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Global environmental change is pushing many socio-environmental systems towards critical thresholds, where ecological systems’ states are on the precipice of tipping points and interventions are needed to navigate or avert impending transitions. Flickering, where a system vacillates between alternative stable states, is an early warning signal of transitions to alternative ecological regimes. However, while flickering may presage an ecological tipping point, these dynamics also pose unique challenges for human adaptation. We link an ecological model that can exhibit flickering to a model of human environmental adaptation to explore the impact of flickering on the utility of adaptive agents. When adaptive capacity is low, flickering causes wellbeing to decline disproportionately. As a result, flickering dynamics move forward the optimal timing of a transformational change that can secure wellbeing despite environmental variability. The implications of flickering on communities faced with desertification, fisheries collapse, and ecosystem change are explored as possible case studies. Flickering, driven in part by climate change and extreme events, may already be impacting communities. Our results suggest that governance interventions investing in adaptive capacity or facilitating transformational change before flickering arises could blunt the negative impact of flickering as socio-environmental systems pass through tipping points.