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As toddlers transition from caregiver-directed regulation to autonomous forms of self-regulation (SR), maternal attempts to regulate toddlers’ emotions and behaviors (MRAs: responses to toddlers’ emotions and behaviors) contribute to development of SR. The aims of this study were to (1) to examine the moment-to-moment effectiveness of MRAs and toddlers’ regulatory strategies (TRS) on within-toddler differences in intensity of expression of negative emotion (ENE) and ability to wait or delay of gratification (DG); and (2) to examine how these effects differed for toddler boys and girls. All study variables were observed during a waiting task and coded in twelve 10s-intervals. MRAs included maternal verbal comfort, distraction, minimizing and punitive responses, and mothers’ own positive and negative emotional reactions. TRS included toddlers’ distraction, task-related verbalizations, and physical behaviors. Toddlers’ ENE was coded as a continuous variable with 0 indicating no expression and 3 indicating severe intensity of expression. Ability to wait was calculated as a frequency of total times toddlers touched or attempted to touch the forbidden toy (higher scores = lower DG). A series of multilevel models with 10s-repeated measurement occasions (n = 1571) nested within 134 mother-toddler dyads (67 girls; Mage = 25.77 months, SDage = 1.60), who were enrolled in the National Early Head Start Research and Evaluation Project, were examined. Toddlers’ current-interval ENE and DG were predicted from lagged (e.g., previous 10s-interval) MRAs and lagged TRS in random coefficient models. Toddlers’ gender was used to explain level-2 slope differences. Multilevel analyses revealed that maternal negative emotional reactions (e.g., becomes upset herself) increased ENE and lowered DG for all toddlers. Maternal positive emotional reactions (e.g., laughs with child) lowered ENE (higher effectiveness for girls), while maternal distraction increased DG for all toddlers. Also, minimizing and punitive responses increased ENE for all toddlers. However, these effects were less robust for boys. In terms of TRS, toddlers’ non-verbal distractions (e.g., looks away from task), and, toddlers’ verbalizations of self-control directed toward mother (e.g., “I wait mama”) reduced ENE, especially for girls. Also, toddlers’ verbal distractions (e.g., singing) (lower effectiveness for boys), and, physical comfort seeking increased DG. These findings provide evidence for effectiveness of maternal and toddlers’ regulatory strategies that partially explain moment-to-moment within-toddler differences in intensity of anger expression and ability to delay gratification when challenged to wait. Findings (a) highlight the role of non-verbal emotional expressions in socialization of emotional and behavioral competence, (b) suggest that girls may be more susceptible to socialization effects of maternal positive emotions, but, that both genders are equally disturbed by maternal negative emotions, and (c) girls use language skills and bids to mother more effectively than boys for self-regulation. The current study’s multilevel modeling analyses of observed repeated-measurement-occasions nested within mother-toddler dyads align conceptual definitions self-regulation as a dynamic and relational construct with the appropriate methodological approaches. These approaches offer nuanced and novel insights in consideration of temporal contingencies and gender effects embedded in socialization of regulatory competence in the context of the parent-child relationship, in particular, for children living in socioeconomic adversity.