The present paper examines the influence of parent's demographics (gender and educational level) and a contextual variable (school grade) on counterproductive parents' behavior during interaction with teachers. Data were gathered by administering the Italian version of the Challenging Parent Standard Questionnaire (Pepe 2010) to a sample of in-service teachers of both elementary and middle schools (N?=?674). As a result, a sample composed of 150 fathers and 524 mothers showing counterproductive behaviors was obtained. General linear model multivariate analysis of covariance (MANCOVA) revealed no statistically significant differences between fathers' and mothers' counterproductive behaviors when controlled for the effects of parents' education and the school grade. Low parental educational levels appeared to be associated with "uncooperative" and "uninvolved" behaviors, whereas "excessively worried" behaviors about a child's education seems to be associated with a parent having a college degree or more. It must be remarked that parents' behaviors can be conditioned by expectation about, or reaction to, the behavior of the teacher and the results should be interpreted by considering nonindependence of involved actors. Results are discussed in terms of theory development and parenting programs aimed at improving parent-teacher relationships.