Legacy Whisperer – Living Docs Powered by Bob

Every software team faces the same silent problem: documentation that lies. A developer updates a function, changes an API response, or modifies a configuration value — and somewhere in a README or API doc, the old information quietly becomes fiction. New developers trust it, get burned, and waste hours debugging something that was never true to begin with. Legacy Whisperer solves this with IBM Bob at its core. When a developer runs git commit, Legacy Whisperer's pre-commit hook automatically captures the diff, parses changed functions, and scans all markdown documentation files in the repository. It identifies which doc sections are potentially affected using intelligent keyword and heading matching — then constructs a precise analysis prompt for Bob. Bob reads the actual code change alongside the documentation and returns exactly which lines are now outdated, why they're wrong, and what the corrected text should be. This isn't keyword search or pattern matching — it's genuine reasoning about what the code change means for human-readable documentation. The Legacy Whisperer dashboard makes the results visual and actionable. Files are marked Critical, Stale, or Healthy. Flagged lines are highlighted directly in a VS Code-style doc viewer. Bob's suggestion appears in a side panel with a before/after diff. One click accepts the fix and writes the correction directly to the file on disk. Legacy Whisperer was built entirely using IBM Bob as the development partner — from scaffolding the CLI to writing the diff parser, designing the React dashboard, and generating the demo repository. Bob wasn't just the product's engine — it was the co-developer that brought Legacy Whisperer to life. The result is a tool that developers would actually use every day: invisible when nothing changes, indispensable when something does.