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 :(
Edit3: neither dropbear for ssh or keyfile worked. I give up.


Security is always about tradeoffs. On my home server unattended reboots are necessary so it needs to auto-decrypt. But using encryption means I don’t need to worry about discarding broken hardware or if I need to travel with the server were it may be inspected. For my laptop, desktop and phone where I don’t need unattended reboots I require the encryption key on bootup.
Thanks, both of your points are good. I was thinking about it in terms of what OP is trying to do. Having key on the same drive. Putting the key on a separate drive or even the cloud like someone else suggested makes sense. I have all of my computers on manual. Since I don’t have anything critical enough that it can’t wait till I’m back home to start it back up.