Legal compliance with local, national and regional privacy requirements is complex and dynamic. Every problem on the local level compounds exponentially when private data is shared across multiple jurisdictions. What data is private, who possess particular data and what laws and regulations apply are by no means transparent. Trans-border communication privacy risks may emanate from sources presumed technologically secure, including the entity’s network architecture and/or application programs. Realization of how vulnerable data is in transit has spurred various, yet unique, technological communication protection solutions. The Internet Protocol Security (IPSec) and Secure Socket Layer (SSL) protocols are two well-known configuration items redressing privacy compliance mandates during information conveyance. However, in-depth security considerations can necessitate transporting messages within a Virtual Private Network (VPN).