Introduction: The dynamic nature of the Internet offers new opportunities for medical learners by presenting several key advantages for the dissemination of medical curricula online. The purpose of this study was to determine technical and pedagogical readiness of faculty and students for the feasibility of offering online medical courses. Methods: This case study was conducted on the main campus of the Universidad San Francisco de Quito (Ecuador) using both quantitative and qualitative methods of inquiry. Data were gathered using online readiness surveys of faculty (10) and students (25), semi-structured interviews with each faculty member, and a focus group interview of eight students. Results: Based on the descriptive statistics and thematic content analysis, faculty and students had positive attitudes toward online courses and overall were prepared in technological readiness. However, the faculty’s knowledge about online teaching pedagogy and instructional design was insufficient. The results also showed several positive aspects of assessing readiness for online education and provided key information for developing solutions to the problems and challenges faculty and students may face in initiating online medical education. Time and budget were reported as the two biggest barriers to develop and implement online courses. Conclusion: Assessing the readiness of faculty and students to participate in online instruction can be challenging, but it is an essential step to get each individual’s input to address common needs and concerns. This process is very helpful in identifying critical success factors, choosing the right approach and applying timely strategies to ensure smooth transitions to new teaching and learning modalities.