When deploying Windows 10 Always On VPN, it may be desirable to host the VPN server in Microsoft’s Azure public cloud. Recently I wrote about Always On VPN deployment options in Azure, and in that post I indicated that deploying Windows Server and the Routing and Remote Access Service (RRAS) was one of those options. Although not formally supported by Microsoft, RRAS is often deployed in Azure because it is cost-effective, easy to manage, and provides flexible scalability.
Supportability
It’s important to state once again that although it is possible to successfully deploy Windows Server with RRAS in Azure to support Always On VPN, as of this writing it is not a formally supported workload. If the administrator makes the decision to deploy RRAS in Azure, they must also accept that Microsoft may refuse to assist with troubleshooting in this specific deployment scenario.
Azure Prerequisites
The configuration of RRAS is identical to on-premises, with a few additional steps required by Azure infrastructure.
Windows Server
RRAS can be configured on any Windows Server virtual machine supported in Microsoft Azure. As with on-premises deployments, Server GUI and Core are supported. Domain-join is optional. The server can be deployed with one network interface or two.
Public IP
A public IP address must be assigned to the VPN server’s external network interface, or the internal interface if the VPN server is configured with a single network adapter. The IP address can be static or dynamic. When using a dynamic IP address, configure a CNAME record in DNS that points to the name configured for the IP address in Azure. If using a static IP address, an A host record can be configured pointing directly to the IP address.
Network Security Group
A Network Security Group (NSG) must be configured and assigned to the VPN server’s external or public-facing network interface that allows the following protocols and ports inbound.
- TCP port 443 (SSTP)
- UDP port 500 (IKEv2)
- UDP port 4500 (IKEv2 NAT traversal)
RRAS in Azure
Below are the infrastructure requirements for supporting Windows Server RRAS VPN in Azure.
Client IP Subnet
Static IP address pool assignment must be used with RRAS. Using DHCP for VPN client IP address assignment in Azure is not supported and will not work. The IP subnet assigned to VPN clients by RRAS must be unique and not overlap with any existing Azure VNet subnets. If more than one VPN server is deployed, each server should be configured to assign a unique subnet for its clients.
IP Forwarding
IP forwarding must be enabled on the VPN server’s internal network interface. Follow the steps below to enable IP forwarding.
1. In the Azure portal, open the properties page for the internal network interface for the VPN server.
2. Click IP configurations in the navigation pane.
3. Click Enabled next to IP forwarding.
4. Click Save.
Routing
Azure must be configured to route IP traffic from VPN clients back to the VPN server. Follow the steps below to create and assign a routing table in Azure.
1. Click Create Resource.
2. Enter “Route Table” in the search field and press Enter.
3. Click Route Table.
4. Click Create.
5. Enter a descriptive name for the route table in the Name field.
6. Choose an appropriate subscription from the Subscription drop-down list.
7. Select the resource group where the VPN server(s) reside.
8. Select the best location to deploy the route table resource from the Location drop-down list.
9. If the administrator wants to have the VPN client IP subnet route information published automatically, select Enabled for Virtual network gateway route propagation.
10. Click Create.
Once complete, follow the steps below to define the route for VPN clients.
1. Open the properties page for the route table.
2. Click Routes in the navigation pane.
3. Click Add.
4. Enter a descriptive name in the Route name filed.
5. Enter the IP subnet assigned to VPN clients in the Address prefix field.
6. Select Virtual appliance from the Next hop type drop-down list.
7. Enter the IPv4 address assigned to the VPN server’s internal network interface in the Next hop address field.
8. Click Ok.
9. Repeat the steps above for each VPN server configured in Azure.
Finally, follow the steps below to assign the route table to an Azure VNet subnet.
1. Open the properties page for the route table.
2. Click Subnets in the navigation pane.
3. Click Associate.
4. Click Virtual network.
5. Choose the appropriate Azure VNet.
6. Click Subnet.
7. Choose an Azure VNet subnet to assign the route table to.
8. Click Ok.
9. Repeat the steps above to assign the route table to any Azure VNet subnet that must be accessible by VPN clients. If VPN clients need access to on-premises resources via Azure site-to-site gateway, assign the route table to the Azure VPN gateway subnet.
Note: Azure only supports the assignment of one route table per subnet. If a route table is currently assigned, the VPN client subnet route can be added to an existing route table, if necessary.
Summary
Administrators have many choices when it comes to support Always On VPN connections hosted in Azure. RRAS on Windows Server can be an effective solution, assuming you can live without formal support. If having a formally supported solution is a hard requirement, consider deploying Always On VPN using the native Azure VPN gateway or another third-part Network Virtual Appliance (NVA).
Additional Information
Azure deployment options
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 
I’m commonly asked “can Windows Server with Routing and Remote Access Service (RRAS) be configured with a single network interface?” This is likely because the official Microsoft documentation references only a multihomed dual NIC configuration, leading many to believe it is a strict requirement.
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.
When deploying Windows 10 Always On VPN using Microsoft Intune, administrators have two choices for configuring VPN profiles. They can use the native Intune user interface (UI) or create and upload a custom ProfileXML. The method chosen will depend on which features and settings are required.
The Windows Server Routing and Remote Access Service (RRAS) includes support for the Secure Socket Tunneling Protocol (SSTP), which is a Microsoft proprietary VPN protocol that uses SSL/TLS for security and privacy of VPN connections. The advantages of using SSTP for Always On VPN is that it is firewall friendly and ensures consistent remove connectivity even behind highly restrictive firewalls.
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.
