An embodiment of the present invention is directed to an automated series of modules to reduce recurring tasks, eliminate manual errors, reduce the firm's risk profile, and decrease time for version upgrades. An embodiment of the present invention is directed to a Technical Debt Automation Tool that determines current and subsequently released versions from a primary vendor as well as for other vendors for various plugins that provide critical business functionality. An embodiment of the present invention may calculate an amount of technical debt (e.g., changes) that an entity (e.g., firm) will have to make due to the customization inherent with firmwide risk policies and AD (Application Development) methodology.