I successfully was able to SSH into my RPi running Ubuntu Core 18.04 installed on a desktop running Ubuntu 16.04. When I attempt to do the same thing on a machine using Ubuntu for Windows 10 after generating my SSH keys, and adding them to my account, I am prompted for a password. The same steps for getting the Ubuntu 16 to ssh into Ubuntu Core were followed.
I found this instance where someone was using a VM: Ubuntu CORE SSH key
However, specifying the file location did not work.
Is there a particular reason why attempting to SSH into the Pi with Ubuntu for Windows is prompting me for a password despite having generated SSH keys while the Ubuntu 16.04 desktop does not.