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This paper analyzes the technical aspects of ERP systems and their connection with agile methodologies, a crucial combination especially in times of economic crisis. ERP system deployments demand resolution to thousands of business process questions and the supporting databases and code base usually have huge numbers of tables and related classes. The complexity is clearly a challenge to manage especially when applying customizations and configurations. We describe how an ERP system’s technical components can be classified from several viewpoints to identify the ones most worthy of investing our time in improving. An upgrade can be worth as much as one-thirt of the initial investment and this agile approach has helped us achieve a productive ERP system development environment, and it has enabled us to perform an ERP system upgrades effectively sometimes skipping an entire version. This provides that an effective connection between ERP deployemnt and agile software can be made to work.