The aim of the study presented is to examine the psychometric properties of two parent–report scales for the assessment of environmental factors in pediatric headache, namely, the Children's Headache Assessment Scale (CHAS) and the Illness Behavior Encouragement Scale (IBES). Data were gathered in a sample of 160 parents of children suffering from headaches regularly. The internal structure of both scales is investigated by means of confirmatory factor analysis. The internal consistency of the resulting subscales is explored and data on the convergent validity and on the relationship with demographics are presented. Both the CHAS and the IBES appear to be promising assessment tools in a behavioral approach to pediatric headache.