Challenging parenting behavior (CPB), a novel construct involving active physical and verbal behaviors that encourage children to push their limits, has been identified as a potential buffer against child anxiety. This study aimed to (a) evaluate the measurement invariance of the Challenging Parenting Behavior Questionnaire (CPBQ4-6) across Dutch and Australian mothers and fathers of preschoolers, (b) examine differences in levels of CPB across mothers and fathers and across countries, and (c) examine whether parents’ CPB predicts less child anxiety symptoms and disorders. Participants were 312 families—146 Dutch and 166 Australian—with their 3- to 4-year-old child (55.8% girls). Fathers’ and mothers’ CPB was measured using the CPBQ4-6, and child anxiety symptoms and presence of anxiety disorders were assessed using maternal reports. Multigroup confirmatory factor analyses revealed equivalence of factor structure and factor loadings (all significant) of the CPBQ4-6 across mothers and fathers and across countries. Evidence of partial scalar invariance indicated that the groups differed on some subscales of the CPBQ4-6. Australian mothers scored lower on the CPB factor than Australian fathers and Dutch parents. Structural equation models showed that CPB predicted fewer child anxiety symptoms and anxiety disorders for all groups. The study confirms that the CPBQ4-6 is appropriate for use with Dutch and Australian parents of preschool-age children and identifies CPB as a multifaceted and coherent construct. The negative relations between CPB and child anxiety suggest that CPB has a protective role in childhood anxiety and is important to examine in future research and interventions.