Best Strategies for Real-Time File Encryption on Windows

Have you checked out Cryptomator? It's a good tool for encrypting cloud storage files, and it focuses heavily on security while being user-friendly. Might be a better fit for what you’re trying to achieve with your cloud backups!

It sounds like you're kind of stuck in an X-Y problem here. First off, you should clarify what you're trying to protect with encryption. If it's data at rest, consider using BitLocker instead. It's robust and user-friendly. If you're specifically backing up, make sure to use a strong passphrase (ideally over 20 characters).

I’m wary of EFS because I've seen users lose access to all their files if their password changes without a recovery key. So, I'd recommend sticking with BitLocker and enabling encryption on any NAS you use. For backups, look for options that encrypt with AES-256. You want something that offers authentication (like AES-GCM) so you can ensure data integrity. If you do opt for EFS, definitely have that recovery key saved offline and set up a data recovery agent on all machines, just to be safe. But personally, I’d steer clear of EFS overall due to its limited use cases.

Just a heads-up: EFS has been largely considered outdated by Microsoft for years now. People often ignore its limitations until it's officially labeled as deprecated, which is a bad sign. You might want to consider alternatives like Cryptomator for more secure file management. It gives better options and flexibility than EFS.