This document discusses the challenges of navigating International Traffic in Arms Regulations (ITAR) compliance on complex international projects like the James Webb Space Telescope (JWST). There are over 130 Technical Assistance Agreements required due to the large number of international partners and subcontractors involved. Full project meetings and data/information sharing require careful registration and documentation to remain ITAR compliant. The Next Generation Integrated Network is the tool developed for JWST to manage ITAR-controlled data. Consistently interpreting and applying ITAR regulations across all entities remains difficult.