To establish the relationship between penetrating complications and bowel luminal narrowing/stricturing disease in pediatric Crohn disease (CD). This retrospective study was IRB-approved and HIPAA compliant with waiver of informed consent. CT and MRI examinations describing intra-abdominal penetrating complications in CD patients ≤18years old between January 1, 2009 and March 31, 2016 were reviewed to document: type of complication, affected bowel segment, minimum bowel luminal diameter, maximum upstream diameter, location of penetrating complication relative to luminal narrowing, length of narrowed bowel segment, and the presence of active bowel wall inflammation. Data were summarized using descriptive statistics including means, standard deviations, as well as counts and percentages. A total of 52 penetrating complications were identified in 45 patients. Mean patient age was 15.7±2.2years (range 11-18years) with 25/45 (56%) boys. Nearly all penetrating complications (51/52, 98%) were associated with a minimum bowel luminal diameter of ≤2mm, with no visible lumen in 26/52 (50%). Mean maximum upstream diameter was 2.8±0.8cm (range 1.2-5.2cm), and 17/52 (33%) penetrating complications were associated with >3cm upstream diameter. The mean ratio of maximum to minimum luminal diameter was 26.2±8.8 (range 3.6-52.0). Active intestinal inflammation was associated with 100% (52/52) of penetrating complications. Nearly every penetrating complication (51/52, 98%) involved the terminal or distal ileum. Penetrating complications in pediatric CD nearly always occur in the setting of considerable luminal narrowing or stricture and active intestinal inflammation.