Pandemic-induced transformations have unevenly impacted local contexts across the globe, mostly depending on technological and social preparedness. Their effect has been particularly significant in Southern European countries, which have historically experienced stark territorial, social, and economic disparities. A striking shift was the rise of remote working, prompting many policymakers to envision a new geography of work. In Italy, remote working was a novel phenomenon for marginalized regions (the South and Inner Areas), affected by low development rates and persistent brain drain flows. Remote working from these areas, termed “south working”, has spurred policy proposals to leverage social innovation and attract human capital within the framework of the European Union Recovery Plan. This chapter examines remote working in Italy’s marginalized areas from an interdisciplinary perspective, by weaving together the analytical issues related to appraising the size of the phenomenon, the legal ones linked to existing and proposed regulations, and the policy-making implications linked to the presence of newcomers in these communities. More specifically, the chapter analyses a comprehensive dataset (2594 entries) of workers’ opinions extracted from a survey by the Italian nonprofit association “South Working”, a map of 230 coworking spaces in marginalized regions, and 18 open-ended surveys with people who experienced “south working” periods. Building on preliminary findings, this chapter advances a series of policy proposals concerning the right to connectivity, transportation, and social infrastructures, with a specific focus on the spread of coworking spaces.