The Autonomous Legacy-to-Cloud Modernization Pipeline solves the massive enterprise bottleneck of manually refactoring outdated monoliths. Using IBM Bob 2.0, this solution orchestrates a multi-step agentic workflow to transition legacy codebases into secure, cloud-native microservices. First, deterministic tools scan the repository to map dependencies without consuming AI tokens. Then, Bob 2.0 enters Plan Mode to design the target architecture. Next, isolated parallel subagents rewrite specific modules, seamlessly converting legacy Java EE servlets into modern Spring Boot APIs and containerizing them with Docker. Finally, dedicated subagents generate comprehensive unit tests and run local validation. This reduces weeks of error-prone refactoring to hours while minimizing token costs.