Parental involvement in children’s education is one of the main components of inclusive education and one of the crucial factors in achieving positive academic outcomes for children with additional support needs (ASN). Using a comparative qualitative methodology, this study explores parents’ perspectives on their involvement in the education of children with ASN attending the lower secondary educational cycle during the COVID-19 pandemic. The study was conducted in Croatia, Serbia and Slovenia—three culturally and educationally similar contexts that applied slightly different educational measures during the pandemic. The study aims to explore the experiences of parental involvement during the pandemic and to gain insights into the personal, familial and contextual factors (level 1 factors in Hoover-Dempsey and Sandler’s model [1995, 1997, 2005]) that influence these involvement practices. Semi-structured interviews with 42 parents of children with ASN from three countries were conducted in the spring of 2022. In all three contexts, the parents intensified at-home involvement and assumed various roles in supporting their children’s learning during the pandemic. Three parental profiles were identified: stable high, intensified and stable low involvement, which were described based on their specific mixture of personal, familial and contextual factors. The results confirm the importance of parental role construction and self-efficacy, the perception of children’s difficulties and the specific invitation from the child, as well as the perception of family life context, in determining parents’ decisions about involvement during the pandemic; however, the results also highlight the crucial role of parental perception of school support for the child.