Always On VPN is infrastructure independent, which allows for many different deployment scenarios including on-premises and cloud-based. In Microsoft Azure, the Azure VPN gateway can be configured to support Windows 10 Always On VPN client connections in some scenarios. Recently I wrote about using the Azure VPN gateway for Always On VPN user tunnels. In this post I’ll describe how to configure the Azure VPN gateway to support an Always On VPN device tunnel.
Limitations
There are a few crucial limitations that come with using the Azure VPN gateway for Always On VPN. Importantly, the Azure VPN gateway can support either user tunnels or device tunnels, not both at the same time. In addition, Azure supports only a single VPN gateway per VNet, so deploying an additional VPN gateway in the same VNet to support Always On VPN user tunnels is not an option.
Root CA Certificate
The Always On VPN device tunnel is authenticated using a machine certificate issued to domain-joined Windows 10 Enterprise edition clients by the organization’s internal Certification Authority (CA). The CA’s root certificate must be uploaded to Azure for the VPN gateway to authorize device tunnel connections. The root CA certificate can be exported using the Certification Authority management console (certsrv.msc) or via the command line.
Export Certificate – GUI
Follow the steps below to export a root CA certificate using the Certification Authority management console.
1. On the root CA server, open the Certification Authority management console.
2. Right-click the CA and choose Properties.
3. Select the CA server’s certificate and choose View Certificate.
4. Select the Details tab and click Copy to File.
5. Click Next.
6. Choose Base-64 encoded X.509 (.CER).
7. Click Next.
8. Enter a location to save the file to.
9. Click Next, Finish, and Ok.
Export Certificate – Command Line
Follow the steps below to export a root CA certificate using the command line.
1. On the root CA server, open an elevated command window (not a PowerShell window).
2. Enter certutil.exe -ca.cert root_certificate.cer.
3. Enter certutil.exe -encode root.cer root_certificate_base64.cer.
Copy Public Key
1. Open the saved root certificate file using Notepad.
2. Copy the file contents between the BEGIN CERTIFICATE and END CERTIFICATE tags, as shown here. Use caution and don’t copy the carriage return at the end of the string.
Point-to-Site Configuration
The Azure VPN gateway must be deployed as a Route-Based gateway to support point-to-site VPN connections. Detailed requirements for the gateway can be found here. Once the VPN gateway has been provisioned, follow the steps below to enable point-to-site configuration for Always On VPN device tunnels.
1. In the navigation pane of the Azure VPN gateway settings click Point-to-site configuration.
2. Click the Configure now link and specify an IPv4 address pool to be assigned to VPN clients. This IP address pool must be unique in the organization and must not overlap with an IP address ranges defined in the Azure virtual network.
3. From the Tunnel type drop-down list select IKEv2.
4. In the Root certificates section enter a descriptive name for the certificate in the Name field.
5. Copy and paste the Base64 encoded public key copied previously into the Public certificate data field.
6. Click Save to save the configuration.
VPN Client Configuration
To support the Always On VPN device tunnel, the client must have a certificate issued by the internal CA with the Client Authentication Enhanced Key Usage (EKU). Detailed guidance for deploying a Windows 10 Always On VPN device tunnel can be found here.
Download VPN Configuration
1. Click Point-to-site configuration.
2. Click Download VPN client.
3. Click Save.
4. Open the downloaded zip file and extract the VpnSettings.xml file from the Generic folder.
5. Copy the FQDN in the VpnServer element in VpnSettings.xml. This is the FQDN that will be used in the template VPN connection and later in ProfileXML.
Create a Test VPN Connection
It is recommended to create a test VPN connection to perform validation testing of the Azure VPN gateway before provisioning an Always On VPN device tunnel broadly. On a domain-joined Windows 10 enterprise client, create a new VPN connection using IKEv2 with machine certificate authentication. Use the VPN server FQDN copied from the VpnSettings.xml file previously.
Create an Always On VPN Connection
Once the VPN has been validated using the test profile created previously, an Always On VPN profile can be created and deployed using Intune, SCCM, or PowerShell. The following articles can be used for reference.
Deploy Always On VPN device tunnel using PowerShell
Deploy Always On VPN device tunnel using Intune
IKEv2 Security Configuration
The default IKEv2 security parameters used by the Azure VPN gateway are better than Windows Server, but the administrator will notice that a weak Diffie-Hellman (DH) key (Group 2 – 1024 bit) is used during IPsec phase 1 negotiation.
Use the following PowerShell commands to update the default IKEv2 security parameters to recommended baseline defaults, including 2048-bit keys (DH group 14) and AES-128 for improved performance.
Connect-AzAccount
Select-AzSubscription -SubscriptionName [Azure Subscription Name]
$Gateway = [Gateway Name]
$ResourceGroup = [Resource Group Name]
$IPsecPolicy = New-AzVpnClientIpsecParameter -IpsecEncryption AES128 -IpsecIntegrity SHA256 -SALifeTime 28800 -SADataSize 102400000 -IkeEncryption AES128 -IkeIntegrity SHA256 -DhGroup DHGroup14 -PfsGroup PFS14
Set-AzVpnClientIpsecParameter -VirtualNetworkGatewayName $Gateway -ResourceGroupName $ResourceGroup -VpnClientIPsecParameter $IPsecPolicy
Note: Be sure to update the cryptography settings on the test VPN connection and in ProfileXML for Always On VPN connections to match the new VPN gateway settings. Failing to do so will result in an IPsec policy mismatch error.
Additional Information
Windows 10 Always On VPN User Tunnel with Azure VPN Gateway
Windows 10 Always On VPN IKEv2 Security Configuration
Windows 10 Always On VPN Device Tunnel Configuration using Microsoft Intune
Windows 10 Always On VPN Device Tunnel Configuration using PowerShell
Windows Server with the Routing and Remote Access Service (RRAS) role installed is a popular choice for Windows 10 Always On VPN deployments. Configuring RRAS is commonly performed using the RRAS management console but it can also be configured using PowerShell and/or netsh. In addition, there are a few different options for natively monitoring server health and client connection status.
The Internet Key Exchange version 2 (IKEv2) VPN protocol is the protocol of choice for Windows 10 Always On VPN deployments where the highest levels of security and assurance are required. However, as I’ve written about in the past, often the 
When configuring Always On VPN, administrators have the option to enable DNS registration for VPN clients. When this option is set, VPN clients will register the IP address assigned to their VPN interface in the internal DNS. This allows client devices to be managed using their hostname from the internal network whenever they are connected remotely.
After deploying or upgrading to Windows 10 1903, administrators may find that Windows 10 Always On VPN connections fail to establish successfully. Always On VPN connections continue to work for Windows 10 1809 and earlier clients, however.
The Windows Server Routing and Remote Access Service (RRAS) includes support for the Secure Sockets Tunneling Protocol (SSTP), which is a Microsoft proprietary VPN protocol that uses SSL/TLS for security and privacy of VPN connections. The advantage of using SSTP for Always On VPN is that it is firewall friendly and ensures consistent remote connectivity even behind highly restrictive firewalls.
Important! Updated July 15, 2019 to support all versions of Windows Server including Windows Server 2012 and 2012 R2. Also added functionality to renew self-signed certificates individually.
