I tried added a key file and even a password txt but both lead to it still asking for me to type in the password.
Is it because the drive is encrypted? I tried placing the files at /, /boot, /root, /etc
Edit1: I’ve tried to install dropbear and give it ssh keys. I will try to reboot in the morning and see what happens
Edit2: signing in via ssh just says port 22 rejected not working :(
Does it really do any good for the drive to be encrypted if it doesn’t require a password (or Yubikey or retinal scan or other authentication factor) on boot? If you’re just going to put the plaintext key/password on the same drive but in a partition that’s not encrypted, there’s no point encrypting the drive, right?
So maybe “it asks for a password on boot” is more of a “works as intended” thing?
The quote above is from Fedora documentation here
This is your root FS that’s encrypted that we’re talking about, correct?
If you really want an encrypted root but no password on boot and the plaintext decryption password/key on the same drive, there are ways to do it. (It would probably require customizing the initramfs somehow. But it’s Linux, and Linux certainly isn’t going to prevent you from doing such things. Just try to dissuade you.)
If we’re not talking about a root filesystem, that would likely change some things. If it’s Luks, I’m pretty sure it wouldn’t matter particularly where on your filesystem the key was so long as your /etc/crypttab refers to it. I’d say that sort of setup would probably only provide additional security if the encrypted drive is an external drive that you might worry could be stolen or physically accessed when the attacker doesn’t have physical access to your root filesystem.
Also, if you shared what encryption scheme was in use (Luks, Anaconda, etc), that would probably help as well.
Edit: Ah. Ok. You gave more info while I was typing the above response. What you want is unlocking via ssh. For sure.