Information and Communication Technology (ICT) advancement has led to the digitization of school selection and placement systems in a developing economy such as Ghana. As a result, the Ghana Education Service (GES) in 2005 introduce the Computerized School Selection and Placement System (CSSPS) to improve selection and placement transparency and equity of Basic Education Certificate Examination (BECE) candidates into Second-Cycle Schools (SCSs), and to reduce the number of human errors connected with the manual system of BECE candidate selection and placement. This study employed a critical realism paradigm and a qualitative method approach underpinned by the Fit and Viability theory to evaluate the CSSPS implementation in a developing economy particularly Ghana since its commencement and determine how well the task and technology match (fit) the demand of CSSPS in addition to its economic factors, IT Infrastructure, and organizational viability have impacted its general performance. Twenty-five (25) respondents were chosen and interviewed based on their level of involvement and the various roles they play in the CSSPS implementation for this study via purposeful sampling. The results revealed that, while the CSSPS was a good fit for the reason for which it was introduced, its viability goals were not fully met. The findings also indicated that CSSPS performance level when introduced was below expectation but has improved over time, hence satisfactory performance. The study extends the fit viability theory beyond IS adoption and implementation to pinpoint the CSSPS's required task and environmental needs, as well as its implementation performance.