The child’s attachment system is complemented by a separate and reciprocal caregiving system in the parent, which guides parents’ protective responses to the child. Disruptions in the caregiving system may lead to disorganized caregiving; however, the study and knowledge of disorganized caregiving is still very incomplete and has been limited to labor-intensive and costly interviews. This study aimed to examine the psychometric qualities of the Caregiving Helplessness Questionnaire (CHQ), a screening tool for disorganized caregiving, on a sample of 200 Portuguese mothers of preschool-aged children. Confirmatory factor analysis did not confirm the structure of the original CHQ version. A five-factor solution was found as a better solution, producing five scales that correspond conceptually to major dimensions of relationship disorganization at preschool-age: Mother Helpless, Mother Frightened, Child Frightened, Child Cheers Mothers, and Child Caregiving. Reliability analysis had satisfactory results and convergent and discriminant validity were confirmed. Concurrent validity was also established by finding significant associations between the CHQ scales with variables of maternal and child domains that have been conceptually and empirically associated with disorganization. In conclusion, results supported the validity of the CHQ for Portuguese mothers of preschoolers, as a promising screening tool for disorganized caregiving.