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Modifying Enterprise Resource Planning (ERP) software to ensure tax regulatory compliance presents complex challenges. The PeopleSoft Tax Update Analyzer uses a three-layer architecture that streamlines the manual review process that traditionally requires extensive specialist involvement. The Input Layer handles the intake of PeopleSoft Tax Update Release Notes and Client Object Repository data. The processing layer applies natural language processing algorithms to analyze release content, with metadata mapping to system modifications. Chain-of-thought reasoning identifies how system modules depend on each other and where conflicts might occur. The output layer generates impact reports that automatically assess which customizations are affected and calculate the testing work required. The framework decreases operational risk from incomplete assessments that preserve organizational knowledge beyond individual employees. Standardized evaluation methods ensure consistency regardless of individual reviewer experience or availability. Implementation outcomes demonstrate that organizations achieve faster regulatory compliance while allocating technical resources more effectively across evaluation cycles. The solution handles problems in systems that contain hundreds of modified objects spread across different functional areas. Systematic automation removes the need for manual reviews while keeping assessment standards high. Organizations can now document their evaluation steps in detail, building knowledge bases that help with future updates and making routine assessments less dependent on specialist staff.