The goal of this study is to examine how to facilitate cross-cultural groups in problem-based learning (PBL) using online digital tools and videos. The PBL consisted of two video-based cases used to trigger student-learning issues about giving bad news to HIV-positive patients. Mixed groups of medical students from Canada and Hong Kong worked with facilitators from each country along with an expert facilitator. The study used AdobeConnect to support the international model through synchronous video interaction and shared applications. This study examines strategies and challenges in facilitating PBL across distance and cultures. Discourse was analyzed using both an inductive and deductive approach where the later used the Community of Inquiry coding scheme. The international context provides a way to facilitate multiple perspectives about how to communicate bad news to patients from different cultural backgrounds. In addition, we present the results of an exploratory analysis of pre and post tests using a standardized patient that demonstrate that the students' pattern of communication showed qualitative change. Several conjectures were developed for future research.