When people think of legacy modernization, most folks aren't imagining the target environment will be Java 8. But this was the challenge facing Nik Malykhin when he needed to run a Java 1.5 codebase on today's hardware. His early use of LLMs gave plausible answers that did not hold up in the codebase. Progress came when he grounded the process in evidence, using AI to support analysis, validation in a stable Docker environment, and gradual refactoring protected by tests. The main takeaway is practical: AI was most useful when constrained by evidence, clear roles, and a step-by-step modernization strategy.