The problem with documentation is that it's an untracked dependency with a slow, manual test procedure. An almost universal example of this is developer onboard

The problem with documentation is that it's an untracked dependency with a slow, manual test procedure. An almost universal example of this is developer onboarding materials that are always (always!) out-of-date. In fact, most teams expect new devs to update the docs as part of their first tasks! (I think this is, in part, to measure a) their ability to deal with bad advice, and b) their willingness to make things easier for those that come after.) It would be great to invalidate documentation when the underlying code changes. There would be two levels of invalidation differentiated by probability: "these docs are definitely wrong now" and "these docs may be wrong and need to be checked." This is easier with APIs than with UIs but I've not seen it done with either. Some motion in this direction are, for example, IntelliJ's comprehensive refactoring support that can and will search documentation. I'm not really sure what a good solution looks like, but there's definitely a chunky problem to be solved here.