This study explored preschool age and gender differences in help-seeking within the theoretical framework of scaffolded problem-solving and self-regulation (Bruner, 1986; Rogoff, 1990; Vygotsky, 1978; 1986). Within-subject analyses tracked changes in help-seeking among 62 preschoolers (34 boys, 28 girls, mean age 4.22 years) solving a challenging puzzle with an adult. The goal was to document whether age and gender interact with fluctuating difficulty to affect children's spontaneous help-seeking. ANOVAs indicated that girls used more help-seeking during difficult segments of the task, despite performance equal to the boys. This pattern was strongest among older girls, who outperformed all other children and used the most help-seeking. Partial correlations, controlling for solving time, indicated that age predicted children's help-seeking during the most difficult segments of the task, but only among girls. Gender differences in social–linguistic maturation and cognitive development are discussed within the framework of Vygotskian theory and related educational practice.