Setting a root password is not enough for Ubuntu 14.04 Server
Edit /etc/ssh/sshd_config
,
sudo nano /etc/ssh/sshd_config
Commend out PermitRootLogin without-password
#PermitRootLogin without-password
Add the following line
PermitRootLogin yes
Set root password and restart SSH service
sudo passwd root
sudo systemctl restart sshd
For 18.04 server
$ sudo sed -i 's/#PermitRootLogin prohibit-password/PermitRootLogin yes/' /etc/ssh/sshd_config