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Migrating a Large Legacy Codebase with AI Coding Agents

Originally published on AI Tech Connect.

What you need to know "Migrate everything" is the failure mode. A large repository does not fit in any agent's context window, so the agent loses the cross-file invariants that keep the system correct and ships code that compiles, reads plausibly, and quietly behaves differently. Characterisation tests come before any migration. Snapshot what the current code actually does, then gate every agent change on those snapshots. This single step is what turns "trust the agent" into "the agent's change is rejected unless behaviour is unchanged". Work in phases with a human checkpoint at each one. Inventory and dependency graph, pilot one module, expand in waves, integrate, cut over — never one giant pull request. Parallelise with isolation, not with chaos. Per-module subagents in their own git…


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