Previous studies of homeschooling focus primarily on two areas: the demographic characteristics and socio-economic status of homeschoolers and the achievements of homeschooled children. Recently, however, the angle of research has shifted to the emotional and social results and emerging problems of homeschooling. Our paper presents the first attempt to investigate the reasons families in Russia choose homeschooling in the context of the historical changes that took place in the Russian education system in regard to the reasons families in Europe and the US choose homeschooling. In addition, this paper identifies the barriers homeschool families in Russia face and ways to overcome them. The study is based on survey data (N = 151) and interviews (N = 33) of parents in Russia. Our results indicate that parents struggle to define their role(s) in their relationships with their children during homeschooling while also encountering a lack of support and the misunderstanding of other family members. In addition to these difficulties, we identified organizational problems, including the transition to homeschooling, the lack of parental pedagogical competence, and the lack of special methods of individual education. A distinctive feature of Russian homeschooling, moreover, is that it remains parent-friendly, allowing the family to choose and organize the form of education for their children, and is developing rapidly while existing being in an institutional environment controlled by the state, with the legacy of the Soviet educational system.