The Internet and especially the Web have effectively become the default mechanism for information dissemination, collaboration, communication and storage. Higher Education institutions have started to make use of these technologies by implementing web based Learning Management Systems (LMS). Their goal is to take advantage of the benefit that web based LMS applications provide by offering their students with a variety of alternative, non-traditional learning methods that may assist the effectiveness of their learning. The paper investigates the effectiveness of implemented LMS applications towards usage of such technologies and subsequently towards learning outcomes from the perspective of students. Data from a university environment was used in order to examine students' usage and evaluation of LMS contents but also to understand from their perspective the state of staff LMS awareness in terms of satisfying their students' expectations. Whilst narrow-focused in terms of respondents, the ability to compare and contrast opinions with actuality provides an interesting insight. eLearning has become a significant method to deliver course materials, while at the same time it is expected to assist students towards reaching the expected learning outcomes, it is important for the academic sector to measure the productivity of LMS implementations from the perspective of their students in order to adopt them in their curricula appropriately. The research provides evidence which recommends that installing a web based LMS followed up by basic technical faculty training will lead in creating module contents that may enhance traditional methods of disseminating course materials offering a more convenient way for students to access it. However, this action alone, will not offer any significant advantage towards the learning objectives of Higher Education, suggesting that a more complete learning strategy needs to be researched to fully utilize the potential of current learning applications.