Background: Assessing insight among OCD-affected youth has been limited by the absence of a multi-item measure for this population. The present study outlines the development of the Measure of Insight for Obsessive-Compulsive Disorder (MI-OCD), presents initial findings, and explores conceptual challenges. Methods: Along with the Children's Yale-Brown Obsessive-Compulsive Scale (CY-BOCS), the 7-item MI-OCD was administered to 178 OCD-affected youth aged 7–19 (mean age = 13.5, SD = 2.8; 55% female) presenting for assessment across three OCD-specialty clinics. Items 4–7 were only completed by those with an identified feared outcome (61%). Results: MI-OCD items were positively correlated with the CY-BOCS’ insight question, but were not related to age or avoidance. Correlations and factor analysis indicated items coalesced around concepts of symptoms as unwanted (1–3) and symptoms as useful/valid (4–7), although factor fit and internal consistency was sub-optimal. Most youth perceived their symptoms as unwanted (positively correlated with severity), while the extent to which youth perceived symptoms as useful was more varied (not associated with severity). Discussion: Insight remains a challenging construct to assess in youth given various developmental, psychological, and environmental confounds. The MI-OCD may be useful in the context of evaluating and addressing individual barriers to treatment engagement over time.