A lot of models and frameworks were suggested to conceptualize and operationalize the e-learning success, and enhance the e-learning and learner performance. Most of these model tries to find out the optimal match among the e-learning components in order to enhance e-learning and learner performance. This chapter explores the e-learning system, its components, e-learning success requirements, opportunities, and challenges that may enable or inhibit e-learning success. As a result, the best fit among the e-learning system components (instructor, learner, course, ICT) is to choose the best mix of the components’ characteristics, as well as taking into consideration the contextual factors (individual, institutional, and environmental) that have a direct impact on the e-learning system components and hence impacts the learner performance. On the other side, institutions must take into consideration the e-learning developments, which take two main directions, mainly; technological, and mechanisms developments. As well as the e-learning challenges which can be classified into technological, individual, institutional, environmental, and educational challenges. To cope with these developments and challenges, an adaptation plan must be formulated at the national level. Where achieving the adaptation plan requires analyzing the global tendencies, the successful applications in the field, and the current local situation.