The Covid-19 pandemic crisis, and the ensuing diffusion of remote work, revived the debate about work meaningfulness, leading many workers to question their hyperconnected worklives. In Italy, this discussion has been animated by the “south working” proposition, which promotes moving towards the south of the country to work remotely and enjoy a slower pace of life and lower costs of living, while contributing to the revitalisation of rural and nonmetropolitan areas. Through digital ethnographic research that employs a variety of data sources, in this chapter I reconstruct the debate around south working across Italian mainstream and social media. I critically discuss the role that hyperconnectivity, disconnection, and digital work lifestyles play in this conversation, reflecting on the significance of the south working proposition in context of new aspirations for a “good life” that are distinctive of the post-pandemic scenario.