Web-based courses are being introduced by higher education institutions at an increasing rate, such that a systematic shift from face-to-face teaching to web-based teaching has become evident. This enthusiasm in web-based education is primarily driven by cost savings and bottom line net profits to institutions. However, research work in the field still has a long way to demonstrate the effectiveness and benefits of web-based learning in general and more specifically, which student can benefit most. Regardless of all the benefits reported, difficulties are still encountered by students, professors, and institutions alike. In fact, many studies show that the web environment for learning is not appropriate for everyone. Therefore, the primary question should be “who is appropriate to take web-based courses?” This of course is in the context of success as it relates to enhanced learning experience and improved performance. Considering the reported benefits and difficulties, this paper identifies seven factors characterizing student success in a web-based learning environment. In addition, we use those factors within a decision support advisory system to help screen students for their appropriateness to take a web-based course. The system was used with few students and this paper reports on one case. The advisory system identifies unfavorable conditions for success to the student and suggests remedial activities to enhance the student’s success.