On login after reseting root password, you could be asked to change password.
When you login via SSH with new password, you’ll see something like:
current Password. You need to enter current one again, and after that two times new one.

Hi @gschnieders, by any chance, did you disabled remote login using root? @xMudrii if that’s the case, will a password reset allow him to login using root?

I had same problem, can not login with root password

I tried reset root password many times, but still can not login

Please help me.

I raises a ticket, but no reply from digitalocean