Regarding dracut-crypt-ssh

Did you remove network from omit_dracutmodules? By default we disable network in the initrd.

Sort of. When you use grub, it is grub that is doing the initial decryption, not dracut.

Under grub, you probably need an unencrypted /boot for that to work the way you want.

You could create a 1GiB ext4 partition and mount it at /boot

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