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The COVID-19 pandemic has impacted the economic market and labor contexts worldwide. Brazil has suffered one of the worst social and governmental managements of the COVID-19 crisis, forcing workers and organizations to develop coping strategies. This environment can affect both well-being and performance at work. Sustainable well-being at work refers to different patterns of relationships between performance and well-being. It may include eudaimonic (e.g., Meaning of Work-MOW) or hedonic (e.g., emotions) forms of well-being. This study tests the moderating role of recovery from work stress in the relationship between flexibility i-deals and patterns of sustainable well-being at work in Brazilian teleworkers. We relied on two studies to achieve this objective. In Study 1, conducted during the pandemic's first outbreak in Brazil ( N = 386), recovery experiences moderated the relationship between i-deals and clusters formed by performance and MOW (eudaimonic happiness). In Study 2, conducted during the second outbreak ( N = 281), we identified relationships between clusters of emotions (hedonic happiness) and MOW (eudaimonic) with performance. The results supported the idea that recovery experiences moderated the relationship between i-deals and patterns of sustainable well-being at work differently. Our findings have implications for Human Resource Management and teleworkers, especially for employee behaviors to deal with stress.