This article contributes to the on-going discussion of parental involvement in the education of children, with emphasis on new and unfamiliar roles of parents during the COVID-19 pandemic. The case study undertaken focuses on parents of first graders who belong to non-vulnerable and vulnerable social groups, and the first-grade teachers of a public primary school in the north of Greece. Research questions address the experience of 'parents-teachers', the need for technological tools and the required digital literacy, as well as the impact of homeschooling on the wellbeing of the family unit. Data were collected using semi-structured individual interviews. The data analysis shows that parents of both social groups took on the role of the teacher to accommodate the learning challenges of first graders. Mothers from vulnerable groups, in particular, encountered various challenges when attempting to support their children mainly in language lessons. Regarding the use of new technologies, the pandemic found parents of both groups unprepared and unfamiliar with the process of distance education. Stress and worry were the dominant emotions from the very start of homeschooling during the early stages of the pandemic while towards the end of the first lockdown, exhaustion overwhelmed parents and pupils. The article concludes with emphasizing the importance of active parental involvement and coaching that enables parents to contribute substantially to their children's education in emergency situations.