Since most of the current literature of system development and implementation are focused on large and complex systems in large corporations, there is a need to study smaller scale system implementation, upgrading, and transformation. This study focuses on small scale system transformation, namely transfer learning management system (LMS) from Blackboard to Moodle at a US university, in order find the similarity and differences between large and small scaled system implementation and transformation. The goal is to identify issues specially related to smaller scale LMS upgrades, and provide insight to IT administrators and administrators of educational institutions.