Thanks to everyone for the suggestions. I wanted to give an update as I am able to connect to the prompt, hopefully will help others who have similar environments similar to mine. My challenge was to get the SSH working from Windows 10 (Surface Pro) where the VM was created in Azure (classic) General guidelines https://azure.microsoft.com/en-us/documentation/articles/virtual-machines-windows-use-ssh-key/ Installed GitHub with GitShell. Ran the command from GitShell to generate the key file and .pem file (openssl.exe req -x509 -nodes -days 365 -newkey rsa:2048 -keyout myPrivateKey.key -out myCert.pem) Installed PuttyGen Convert to .rsa file so PuttyGen can understand (openssl rsa -in ./myPrivateKey.key -out myPrivateKey_rsa# chmod 600 ./myPrivateKey_rsa) Load the private key via PuttyGen, save the PrivateKey as .ppk file Next copy the PublicKey from PuttyGen. Now, I attempted to take the key to existing Azure VM, Settings, Reset Password and change to SSH Public Key. Although, the key was accepted, it did not finish for a long time. The restart did not help. Kept getting Server key was refused. So, I created a new VM using Marketplace Sandbox using Resource Manager (not classic) using the Public Key. Note down the user name! Ran Putty, provided the IP address using port 22, on SSH -> Auth page, provided the .ppk file saved earlier from PuttyGen. When prompted, provide the username used in Azure portal. Voila! ... View more