Objective. Longitudinal associations among maternal personality, emotional expressions, and parenting were examined. Design. Maternal parenting (sensitivity and intrusiveness) and positive emotional expressions were observed during a free-play session with toddlers at 18 (T1, n = 246) and 30 (T3, n = 216) months. Mothers completed a personality measure at T1 and a questionnaire measuring their emotional expressiveness (positive and negative) when toddlers were 24 months old (T2, n = 213). Results. Dimensions of maternal personality and maternal emotional expressiveness were related to individual differences in maternal parenting behaviors, in particular to maternal sensitivity. Conscientiousness and Agreeableness at T1 were positively associated with observed positive emotional expressions at T1. Agreeableness, Openness to Experience, and Extraversion at T1 also were positively related to positive emotional expressions reported by mothers at T2. Maternal positive emotional expressions (T1 and T2), in turn, were associated with more sensitive behavior observed with toddlers at T3. Conclusion. In addition to direct effects of maternal personality on maternal parenting, mothers' emotional expressiveness was found to be a possible pathway for explaining relations of maternal personality and parenting.