Parental monitoring has been defined as "a set of correlated parenting behaviors involving attention to and tracking of the child’s whereabouts, activities, and adaptations." This construct is of significant interest due to its relatedness to a broad range of youth risk behaviors, including risky sexual behavior, substance abuse, and poor adherence. However, to date, measures of parental monitoring are largely absent from the chronic illness literature. The present article focuses upon two key problems in the operationalization of the monitoring construct to date: (a) poor conceptual specificity in parenting constructs such as monitoring, overprotection, and over-involvement when used to date among youth with chronic conditions and (b) the confounding of existing measures of parental monitoring with items evaluating parental knowledge of youth activities, which has resulted in a lack of data regarding the mechanisms by which parents obtain their information. Recommendations for the future development of monitoring measures are discussed.