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This article explores the tension between self-directed education in democratic schools in the Wallonia-Brussels Federation (FW-B) and the legislative framework governing homeschooling, which families are required to follow. Although these schools promote self-directed learning, FW-B monitoring raises concerns among parents regarding their children’s skill acquisition, sometimes prompting reintegration into the traditional school system. Drawing on semi-structured interviews with project leaders from four democratic schools, the study examines the strategies developed jointly by schools and families to reconcile educational values with legislative requirements, while also highlighting the instability of these schools when confronted with parental expectations.