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Toddlerhood is a period where issues of autonomy and control in parent–child relationships become particularly intense. In response to these challenges, some parents adopt controlling practices, whereas others are more autonomy supportive. However, research has yet to examine prenatal orientations that foreshadow specific controlling or autonomy-supportive parental practices in toddlerhood and children's socioemotional functioning. In particular, literature on early childhood socialization lacks sufficient evidence on the effects of the controversial controlling practice of parental conditional positive regard. To increase our knowledge on these issues, we examined reports provided by Israeli Jewish mothers during their first pregnancy (N = 294), at 18-month postpartum (N = 226), and when the child was 42 months old (N = 134). To control for child temperament, both parents reported 8-month postpartum (N = 235) on infant temperament dispositions, which may act as precursors of later socioemotional functioning. Structural equations modeling revealed that a general prenatal maternal orientation to use conditional regard as a socialization practice predicted mothers' use of the specific practices of conditional positive and negative regard with toddlers, which then predicted internalizing problems when children reached the age of 42 months. Additionally, a general prenatal orientation toward autonomy-supportive parenting predicted mothers' perspective taking with toddlers, which then predicted children's prosocial behavior at 42 months. The effects emerged also after controlling for infants' temperamental dispositions toward negative emotionality and positive affect. Findings underlie the potential role of prenatal orientations toward conditional regard and autonomy support that, when later transform into specific early parenting practices, may serve as early markers of child socioemotional adjustment. [ABSTRACT FROM AUTHOR]