The widespread use of digital technologies such as smartphones, tablets, and notebook computers expose firms engaged in international business to risks that far exceed what most corporate technology users understand. This case study examines some of the technology-specific vulnerabilities managers face when engaged in international travel and introduces tools and technologies including HTTPS, two-factor authentication, VPNs and the use and management of complex passwords. The case concludes with a set of discussion questions and hands-on exercises that can be completed in or out of class. This case is intended for the Intro to MIS class and complements the model curriculum objectives in IS 2010.1 and IS 2010.7.