Organizations have been making in the last years heavy investments in Web-based distance learning initiatives. Despite the many uncertainties that this involves, part of the teaching and learning processes are moving towards the Internet. These uncertainties bring about difficulties for managers, who face the challenge of keeping the focus on essential and relevant aspects that will assure programmes success. However, what would these factors be? This article aims at answering this question by identifying the critical success factors of Web-based distance learning programmes. With this objective, nine semi-structured interviews with experts were held and two case studies were carried out. Results point to the existence of five critical success factors, namely (1) the experience and background of the program teams, (2) the students’ characteristics and behavior, (3) the learning model, (4) the technology and (5) the establishment of strategic alliances.