Evaluating e-learning is an important measure for quality control, which aims to improve the whole e-learning environment through taking into consideration users’ perceptions and needs, as well as participants, stakeholders, and institutions. However, literature does indicate that institutions are only using e-learning as a repository for uploading academic materials, instead of taking into consideration of features and the learner. This chapter examines a variety of evaluation techniques adopted from e-learning, personalised learning, and User Modelling to suggest improvements within the industry to challenge the end users’ perceptions of on-line education.