Todays’ institutions of higher learning faced with a problem of facilitating learning with a changing profile of students, in bigger and bigger classes. The environment in these institutions is undergoing major changes as many academic institutions are offering courses either partially (Web enabled) or totally (Web exclusive) online to facilitate learning. Most recently, Virtual Learning Systems has become an important feature of electronic service delivery within institutions of higher learning and in response demanding close attention to issues of functionality, sustainability and usability. In this paper we discuss usability of VLS and the associated antecedent characteristics. A field study was employed to get feedback from lecturers and students in one of the universities in Kenya as a case. From the study, we propose keen attention to be given to three usability characteristics: understandability, learnability and operability from the user’s perspective.