A way for it to know is to build a maintenance loop around the context. Technical changes are relatively easy to track. A system can monitor code diffs, schema

A way for it to know is to build a maintenance loop around the context. Technical changes are relatively easy to track. A system can monitor code diffs, schema changes, failed queries, etc and update or flag the affected context. Business meaning changes are harder to detect, but users reveal them whenever they use the agent: through the questions they ask (and that the existing context cannot answer), the ambiguities it encounters, and the corrections or clarifications they provide. Your maintenance system can capture those signals, connects them to the relevant parts of the context, and proposes an update.