Technical debt from outdated dependencies can quietly destabilize even the most robust applications. This talk explores a proactive approach to tackling this issue within CI/CD pipelines. By leveraging tools like the Maven Versions plugin for automatic version detection and the Enforcer plugin to enforce upgrade policies, we created a process that ensures continuous updates while maintaining stability. Attendees will learn how to streamline dependency management, enforce build failures for outdated libraries, and balance innovation with long-term security—keeping their codebase agile, secure, and up-to-date.