Understanding Azure Linux VM Authentication with SSH Key Pairs

The best and most secure option for authenticating to an Azure Linux VM is with a private & public key pair. It is possible to configure password authentication during the deployment of a VM, but this could be subject to a brute-force attack. A private & public key pair is used to secure the authentication, the Azure Linux VM has the public key and the administrator’s workstation stores the private key. It is possible to use the same key pair to authenticate to multiple Azure Linux VM instances, any most do.

I am going to start by deploying a new Ubuntu instance as an Azure VM, from the deployment I am going to select SSH Public Key for the authentication type. For certificate-based authentication you must still specify a username, in this example I have went with AzureUser. I have also selected the option to generate a new key pair as part of this deployment. This key pair will become my primary set of keys to authenticate to all my Azure Linux VM instances, so I have given it a descriptive name. 

Continue through the rest of the wizard to deploy a new Azure Virtual Machine. Once you get to send and you push the configuration to Azure Resource Manager in the form of a deployment you will be faced with this. You must select the option to download the private key as Azure does not store this for you. If you fail to download the private key at this stage this key pair will be null and void. 

The default format is PEM when you generate a key pair directly from Azure. This is what format the private key is downloaded in. If you want to authenticate to Azure Linux VMs using Putty you will have to convert the PEM file to PPK, or authentication will fail. To do this the PuttyGen tool can be used. The first step is to import the private key PEM file from Azure. 

Once successfully imported you must then use the Save Private Key option to ensure you end up with a PPK file which Putty can parse for authentication. 

Once you have a PPK version of the private key, you can use Putty to authenticate to the Azure Linux VM. Do not forget you must point to the PPK file from inside Putty under SSH > Auth.

Ok so we have covered how to deploy a new Azure Linux VM with a new key pair, convert the private key to a form in which Putty can use and authenticate to a VM.

The next step is to configure other Azure Linux VM’s to use this key pair for authentication. A new resource is created in the Azure Resource Group in which the next Azure Linux VM was deployed, this resource is an SSH Key. This is the public key side of this key pair which can be configured on other VM instances. If you query the SSH Key, we can copy and paste the key itself. 

Now if we want to update existing VMs to use the key pair we can go to the VM and under Reset Password select thee Reset SSH Public Key option. From here we paste in the new public key which was created as part of the original VM. 

Once this has been committed, we will be able to use out master private key to authenticate to this Azure Linux VM.