> Regardless of where it is, something should know to include it in the context,

Magic. You're talking about magic. You keep re-iterating the same faith that "There's some magic way to make probabilistic text generator running in the cloud to never miss local files", where "files" is "files, knowledge graphs, databases etc.".

It doesn't matter how data is stored. You can't know when to include something relevant in the context because the whole thing including context is running in the cloud. You are not in the driver's seat. Literally anything you include locally in the prompt can and will be ignored.