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How to Establish a VPN Point to Site Connection in Azure

Sven Malvik Sven Malvik Connect Dec 17, 2020 · 5 mins read
How to Establish a VPN Point to Site Connection in Azure

I will demonstrate how to establish a point to site connection in Azure, and connect from a Windows workstation to a virtual machine via its private IP address. Azure Point to Site Connection is part of the AZ-303 exam for becoming an Azure Solution Architect.

Watch Azure Point to Site VPN ConnectionWatch Azure Point to Site Connection in preparation for the AZ-303 exam

Sometimes we need to have our workload running on a virtual machine with no public IP address. At the same time we want to connect to it from our workstation. In the picture below I created already a Windows 10 Client workstation in the West Europe region. In the Central US region I created a virtual network with another vm, Windows Server 2016 Datacenter. I did not assign a public IP address to it, so it has only a private IP address. I also installed the Internet Information Server (IIS) on it. Right now it’s only accessible from localhost and within this virtual network.

Pre-provisioned Azure resourcesPre-provisioned Azure resources

Our goal is to create what’s described below.

  1. Create a subnet gateway. The name SubnetGateway is important as it will be recognized as such of the virtual network gateway in the next step.
  2. Create the virtual network gateway.
  3. Generate the root certificate and client certificate.
  4. Setup the point to site connection with the root certificate.
  5. Establish a connection from the client workstation to the server.

Architecture for point to site VPN connectionArchitecture for point to site VPN connection

We start by adding the subnet gateway. You find it under Subnets within your VNet. The name GatewaySubnet is important, and you can’t change it. I leave the address range as it but feel free to give it a smaller range i.e. /27.

Creating Subnet GatewayCreating Subnet Gateway

Now that we have the subnet gateway in place, we can create a virtual network gateway. Create Virtual Network GatewayCreate Virtual Network Gateway

We set the gateway type as VPN, and the VPN type as Route-based. The subnet is set automatically to your subnet gateway. That’s why the name is important.

Azure Virtual Network ConfigurationAzure Virtual Network Configuration

If we scroll down a bit a must not forget to name a public IP address that we need for establishing a VPN connection. We won’t use it directly for accessing the IIS.

Azure Virtual Network Configuration Public IP addressAzure Virtual Network Configuration Public IP address

Now we need to create some certificates. First we need a root certificate. Your organization may already have one. Out of this root certificate, we create a client certificate that we need to have on the workstation.

First, login to the client workstation and open Powershell. Run the first command for the root certificate.

$cert = New-SelfSignedCertificate -Type Custom -KeySpec Signature -Subject "CN=RootCertificate" -KeyExportPolicy Exportable -HashAlgorithm sha256 -KeyLength 2048 -CertStoreLocation "Cert:\CurrentUser\My" -KeyUsageProperty Sign -KeyUsage CertSign

Then run the following command for creating the client certificate out of the root certificate.

New-SelfSignedCertificate -Type Custom -DnsName P2SChildCert -KeySpec Signature -Subject "CN=ClientCertificate" -KeyExportPolicy Exportable -HashAlgorithm sha256 -KeyLength 2048 -CertStoreLocation "Cert:\CurrentUser\My" -Signer $cert

You can see the result below.

Creating self-signed certificates with PowerShellCreating self-signed certificates with PowerShell

Search now for rootcert and right-click on it to open it with Notepad or any other text editor.

Search for RootCertSearch for rootcert

Read root certificate with NotepadRead root certificate with Notepad

Select the content of the root certificate so you can copy it.

Copy content of root certificateCopy content of root certificate

We head back in to the Azure portal and to the virtual network gateway. In the menu is the Point to Site Connection that we will open. The Point to Site Connection will represent your workstation. Set the address pool of it and then the tunnel type IKEv2 and SSTP (SSL). Then, we set the value of our root certificate as shown below.

Last, we download the VPN client on to our client workstation. I simply logged in to Azure from the client workstation and downloaded the VPN client from there.

Configuring Point to Site ConnectionConfiguring Point to Site Connection

Extract the downloaded file and run it. It will install the VPN client on the workstation.

Install VPN clientInstall VPN client

Search for VPN settings and open it.

VPN settingsVPN settings

Now we can connect to the virtual network of the server.

Connect to virtual networkConnect to virtual network

I checked the private IP address of the virtual machine running the IIS, 10.0.0.4. We open a browser, and vóila. We can access the IIS from our client workstation with a private IP address.

Access IIS with private IP addressAccess IIS with private IP address

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Sven Malvik
Written by Sven Malvik