Over the years, organizational training plays an important role in human resource management in firms and organizations. With the rapidly changing technology and the increasing business demands, organizations especially IT departments have been investing greatly in web-based training. However, a successful web-based training system depends not only on the willingness from management, but also on IT infrastructure and employee acceptance, which is determined by many factors such as the degree of courseware customization and the level of collaboration. In this study, propositions on the critical success factors of a web-based training system were raised and verified in a case-study involving two web-based courses in a large corporate IT department. The case study method is used to contrast between two modules, and demonstrate the critical success factors for the web-based IT training in a corporate environment. Four factors were identified including management involvement and support, courseware customization, level of collaboration and effective and consistent IT infrastructure. The insights gained and lessons learnt from this case study may hold valuable implications for both research and practice.