The relation between maternal behavior and neurocognitive development is complex and may depend on the task context. We examined 5-month-old infant frontal electroencephalogram (EEG), maternal intrusiveness (MI) evaluated during two play contexts at 5 and 10 months, and a battery of executive function (EF) tasks completed at 48 months to evaluate if MI during infancy and infant neural function interacted to predict later cognition. Infant frontal EEG was a predictor of 4-year EF. MI during structured play at both 5 and 10 months predicted preschool EF, and MI during unstructured did not have a main effect on EF but showed a potential moderating effect of infant EEG on later EF. The pattern changed between ages, with MI during structured play at 5 months showing a positive association with age 4 EF, whereas MI during structured play at 10 months had a negative association with age 4 EF. We demonstrate differences in the context of maternal behavior used to predict childhood EF, highlighting the importance of considering parenting context in EF development.