Every instructional process involves a strategic assessment system for a complete teaching-learning circle. Assessment system which is seriously challenged calls for a change in the approach. The National Open University of Nigeria (NOUN) assessment system at present is challenged. The large number of students and numerous courses offered by NOUN as an open and distance learning institution make assessment very cumbersome and an administrative nightmare. This paper has employed descriptive approach in studying the nature and various directions of challenges associated with NOUN assessment. These challenges are related to conduct of examination such as question paper, finance, manpower, collation of results and release of meaningful results. The study explores how technology envisaged to ameliorate these challenges can effectively be employed to restructure assessment in NOUN. Issues relevant for effective deployment of technology in restructuring like question bank, logistic operations, operational processes of technology and formal registration of students for assessment are discussed for ease of implementation. Implications for the use of technology in assessment are presented. Cogent recommendations are made for effectiveness of the system. In sum, the deployment of technology is a viable sustainable strategy open to NOUN to effectively manage the burden of assessment of students' learning outcomes.