Digital applications have been vital to ensuring business continuity during the COVID-19 pandemic. Indeed, digital transformation is considered key to shaping Europe's future, including the opportunity for hybrid work. Consequently, a central issue is the experience and perception of workers and the effect on their mental well-being. Building on the assumption that the more 'digitalized' and 'experienced with working from home (WFH),' the more positive peoples' perceptions are, this paper explores how workers in Italy and Denmark perceived WFH during the first COVID-19 lockdown from a psychosocial perspective and what lessons could be drawn for policy and industry. Ranking top and bottom respectively on the European Digital Economy and Society Index (DESI) and different pre-pandemic experiences of WFH, data about WFH perceptions and mental well-being were collected among Danes and Italians via a survey from March to May 2020. The data were analyzed using descriptive statistics, t-Tests, and ANOVA. The combination of high rank and pre-experience of WFH did not result in a positive perception of WFH. Mental well-being of Danes were mostly affected and they experienced WFH to be more challenging than the Italians, where the key disadvantages were related to "Home office constraints" and the isolation that followed. When digitalizing Europe and workplaces are likely to offer people the opportunity to have hybrid work, the results highlight how national conditions affect the prospects of the new ways of working including people's mental well-being and where actions are most needed for policy and industry.