arXiv:2611.05457v1 Announce Type: new Abstract: Large organizations carry a long tail of infrastructure migrations that are worth doing but rarely urgent enough to compete with feature work, because each one costs significant engineering time per repository. This paper reports on our industrial experience from Automated Uplift, a multi-month initiative applying LLM-assisted migration pipelines across thousands of Bloomberg repositories. We examine two distinct production campaigns: a heterogeneous Python packaging migration (approx. 1,900 candidate repositories) and a uniform C++ build system migration (approx. 6,700 candidate repositories). Together, these campaigns generated 2,333 pull requests, resulting in 729 successful migrations. We detail our hybrid architectural solution which maximizes deterministic processing, confines the LLM to bounded file transformations within a pre-computed context, and incorporates runtime production telemetry (such as execution logs and usage traces). Our findings show that generating migrations turned out to be the easier part; the bottleneck was the cost, for owning teams, of reviewing, testing, and deploying them. These costs were lowered when changes could be verified directly in the pipeline before opening a PR (as with C++ compilation and test validation), and when the population was uniform enough for fixes to carry over from one repository to the next. We conclude by distilling our experience and findings into actionable, transferable patterns for architecting hybrid LLM-deterministic pipelines and scaling code migrations across the enterprise