The ySKILLS project seeks to better understand which skills 12- to 17-year-olds must obtain to knowingly and critically use Information and Communication Technology (ICT) for their wellbeing, education and social life, and to improve existing knowledge about how children and youth can build resilience against negative impacts. This report is part of the Work Package 3 ‘Digital Skills: Actors and Factors’ and aims to contribute a deeper knowledge of home-school collaboration in developing digital skills. Within the framework of WP3, 34 in-depth interviews with experts from the education sector and the labour market were carried out in Estonia, Finland, Germany, Italy, Poland and Portugal, with the aim of getting a deeper understanding of (1) the (digital) skills that youth need in the 21st century, and (2) the role of digital skills education, both in formal (e.g. the school) and informal learning settings (see Deliverable 3.1 by Donoso et al., 2020). This report is based on 20 interviews with education sector experts: teachers and headmasters; researchers, lecturers and professors; education specialists and policy makers – who were part of the whole sample of 34 experts from six European countries as mentioned above. This report provides insights into the opinions and views of education experts on the most relevant problems in the collaboration and communication process between homes and schools that should be discussed, acknowledged and dealt with, in order to foster cooperation instead of confrontation. As a result of their professional and personal experience, the participating experts were able to provide deep insights into the complexities of home-school communication and explain what (side) effects these have on young people’s digital skills. Their views are, therefore, a valuable resource providing evidence-based recommendations and strategies for key stakeholder groups to promote closer partnership between home and school, in order to support children’s better communication and digital skills and wellbeing. Many of the interviewed experts highlighted that despite the fact that digital skills have increasingly become an integral part of people’s lives, there are still many shortcomings in aspects of communication between home and school. As the interviews were carried out in April and May 2020, amidst the first wave of the COVID-19 pandemic in Europe, many of the interviewees reflected on how this crisis and the consequent ‘social distancing’ had impacted education and home-school communication, when, all of a sudden, learning and working had become essentially digital. Several experts noted that this crisis has exemplified how unequally prepared and equipped families are to benefit from the distance learning that was put in place during the period of restrictions.