Selfhosted
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This answer here covers it quite nice imo.
https://unix.stackexchange.com/questions/5017/ssh-to-decrypt-encrypted-lvm-during-headless-server-boot
Important is that you update your initramfs with the command after you edited the dropbear initramfs config and or you copied the key over.
For the client it is important to define 2 different known hosts files since the same host will have 2 different host keys, 1 when encrypted with dropbear, and 1 when operational with (usually) sshd.
Also you need to use root when you connect to your server to unlock it. No other user will work with the default setup.
I was actually using my own user account instead of root, but now that you mention it… I’m not sure how that would even work so yeah that makes sense.
I did rebuild the initramfs after every change but did not manually copy the key file anywhere other than etc.
Will check out the link tomorrow. Thanks a lot for sharing!
Edit: tried again with root and it worked flawlessly :D