The case study demonstrates the detailed steps of selecting Enterprise Resource Planning (ERP) software which transforms the business transactions of a company, Enigma Systems Ltd., enabled by information Technology. The protagonist of the case study, IT Director, Abhay Kishore, heads the team for selecting the right ERP for the business at Enigma. The case study highlights the pain point of the company operations and demonstrates the decision-making process for ERP selection along with all the considerations. The case study touches upon the key aspects like that of need for ERP, core team formation and deciding the apt ERP. The case study also gives the ground reality of the struggles faced by the team in process of selection and evaluation for fitment of an ERP system. ERP system is not only a farsighted strategic investment for the company it also impacts every business process from Finance, Supply Chain, Distribution, Purchasing, Inventory, Manufacturing, Customer service to HR Departments and its employees. The case study highlights the various aspects, considerations and processes that can help ascertain the best fit ERP. The case study also highlights the challenges faced by IT and core ERP selection team in its pursuit for the right fit ERP for its processes.