The present research explored how mothers' own childhood experiences are linked to their perceptions of their children's sleep regulation. It focused on collective sleeping; a practice used in the past in the Israeli kibbutz, and used a quasi-experimental research design to examine whether mothers who were raised in collective sleeping arrangements differed from mothers who were raised in home sleeping. Two typically developing cohorts: infants (n = 68; ages 9-15 months; M = 12.2, SD = 2.2) and preschool children (n = 113; ages 48-55 months; M = 51.5, SD = 1.85) participated in this investigation. Sleep regulation and temperament were reported for infants and children, whereas for mothers data were collected on separation anxiety and appraisal of the ecology in which they were raised. Collectively raised mothers evaluated their upbringing significantly more negatively than home-raised mothers, expressed higher separation anxiety with regard to an alternative caregiver, but were not different in their views of their child's sleep difficulties. For infants, it was maternal separation anxiety that contributed uniquely to the explained variance in maternal view of sleep regulation difficulties. For preschool children, it was maternal evaluation of own childhood ecology and child's temperament that contributed uniquely to the explained variance in maternal view of sleep regulation difficulties. These findings suggest that mothers' representations of their sleep-related early experiences, rather than their childhood ecology in and of itself, influenced their perceptions about their child's sleep, which, in turn, affect child's sleep patterns. Implications to caregiving are discussed. (Contains 4 tables.)