Patients with inflammatory bowel disease (IBD) have a greater risk for developing venous thromboembolism (VTE). Patients admitted to the hospital with IBD flares often require insertion of long-term venous access devices, such as peripherally inserted central catheters (PICCs), to provide access for medications, blood draws, fluid management, and nutrition. PICCs have been associated with an increased risk for upper extremity deep vein thrombosis. In this case study analysis, 2 patients with IBD and PICCs who developed VTE are examined. The case report includes a thorough discussion of medical history, symptomology, PICC insertion, and events leading to VTE development. A review of acquired risk factors for IBD patients and a comparison of risk factors that predisposed each to VTE are explored. These cases highlight the need for nurses and physicians to heighten surveillance and engage in proactive strategies to prevent VTE in this population of patients.