University curriculum all over the world contain a set of learning outcomes to be achieved through different learning and teaching modes. The achievement of the Learning Outcomes is measured using some form of assessment, usually in the form of University examinations. The traditional teaching has been face-to- face, and therefore many examinations have also been conducted in a face to face manner. One of the challenges of any examination setting is cheating amongst University students, which implies that the examinations must be properly invigilated or proctored. Since the introduction of ICT in Education, there have been attempts to introduce Online examinations, although these are yet to gain full traction. In Kenya, the ODEL standards lean more towards blended learning, where each course has to have a face to face element. Many Universities have therefore been conducting their examinations in a traditional setting. The onset of COVID-19 created a different situation as the social distancing and the restricted movement meant that learners could not attend a physical class. The movement to Remote Emergency Teaching created a challenge on how examinations could be conducted and proctored. Several Universities decided to do the teaching but wait for resumption of face to face studies to conduct their exams, and this had a negative impact on the University Almanac. This paper looks at the case of one Private University that decided to complete a whole semester online but also went on to conduct examinations via the Learning Management System. Using a triangulation of Interviews, Observation and Document Reviews, staff and students who had participated in conducting and taking online examinations were interviewed. The online examinations processed was observed and documents and software used in online examinations and proctoring were reviewed. Reorganization of the examination processes, organizational and cultural change management, ICT technical issues, extensive training, software selection and communication were identified as the key requirements for successful online examinations and proctoring to take place. The use of Proctoring Systems that are integrated with the LMS give a shorter learning curve and are easier to learn and use.