Is there an idiomatic way to have Flask reload my configuration file on every request? The purpose of this would be so that I could change passwords or other configuration r
You cannot safely / correctly reload the config after the application begins handling requests. Config is only meant to be read during application setup. The main reason is because a production server will be running using multiple processes (or even distributed across servers), and the worker that handles the config change request does not have access to other workers to tell them to change. Additionally, some config is not designed to be reloaded, so even if you could notify all the other workers and get them to reload properly, it might not have any effect.
Production WSGI servers can gracefully reload, that is they won't kill running workers until they've completed their responses, so downtime shouldn't actually be an issue. If it is (and it really isn't), then you're at such a large scale that you're beyond the scope of this answer.
Graceful reload in:
If you need to use config that can be updated dynamically, you'll have to write all the code you use to expect that. You could use a before_request
handler to load the config fresh each request. However, keep in mind that anything you didn't write that uses config may not expect the config to change.