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I'm using https://github.com/dracut-crypt-ssh/dracut-crypt-ssh on some of my servers. The initrd opens an ssh port where you can login and enter the passphrase. Setting it up is non-trivial, but it works well. Haven't tried it on Debian but there should be something similar.
This is actually really interesting, I might have to try this.
I currently use a USB stick with a key file on it that I need to plug in on boot. Something like this but it wasn't that easy for me. https://openterprise.it/2022/07/fedora-unlock-luks-full-disk-encrypted-system-using-usb-stick/
Edit: I wonder if yours will work on my VPS.... I'd love to encrypt that.