Considerations for Always On VPN with Azure VPN Gateway and Virtual WAN

Always On VPN Device Tunnel and Custom Cryptography Native Support Now in Intune

Organizations migrating on-premises applications, data, and infrastructure to the cloud may also consider terminating Always On VPN connections there. Using one of the native Azure VPN services might be compelling at first glance. After all, having an Azure-managed VPN gateway service sounds intuitive. However, some severe limitations exist for using Azure VPN services for Always On VPN deployments.

Azure VPN Gateway

The following are limitations for Always On VPN with Azure VPN gateway.

Authentication Methods

Azure VPN gateway supports both EAP and machine certificate authentication. However, it can only support one authentication method at a time. With only EAP or certificate authentication, administrators must choose between a device or user tunnel. A single Azure VPN gateway cannot support both at the same time. For native Entra ID joined devices, this is not a problem. However, for native on-premises Active Directory or hybrid Entra ID joined devices, this is a problem, as the device tunnel is essential in these scenarios.

Note: Technically speaking, administrators could deploy another Azure VPN gateway to work around this limitation. However, Azure limits VPN gateway deployments to one per virtual network. This requires administrators to deploy a second VPN gateway in a separate virtual network, which then requires virtual network peering to be enabled, complicating the configuration greatly.

SSTP

Although the Azure VPN gateway supports SSTP, it is, unfortunately, a second-class citizen. Today, all SKUs of the Azure VPN gateway are limited to just 128 SSTP connections (256 in active/active mode). There is currently no way to increase this. If more than 256 connections are required, you must use IKEv2.

RADIUS

In addition, there is currently no option to change the default timeout value (30 seconds) for RADIUS authentication requests. This short timeout value presents a challenge when using MFA with the NPS extension or with Azure Conditional Access, as users may be unable to respond to the push notification before the timeout expires, resulting in failed authentication attempts.

In addition, Azure does not support routing traffic to on-premises RADIUS servers over ExpressRoute connections. In this scenario, administrators must route RADIUS traffic to on-premises servers over a site-to-site connection.

Geographic Redundancy

Geographic redundancy using Azure Traffic Manager (or another global server load balancer) with two or more gateways is not supported when using the Azure VPN gateway. Azure manages the certificate used on the gateway, which includes a certificate with the subject name of the individual gateway. There is no option to supply a custom certificate with a global hostname in the subject, which is required to support geographic redundancy. With that, administrators are limited to the redundancy provided natively by the Azure VPN gateway.

IPv6

Azure does not support Azure VPN gateway in a virtual network that includes IPv6 addressing.

Azure Virtual WAN

Azure Virtual WAN includes many of the same limitations as the Azure VPN gateway, in addition to the following.

SSTP

Unlike the Azure VPN gateway, there is no support for SSTP in Azure Virtual WAN.

IPv6

IPv6 is not currently supported at all in Azure Virtual WAN.

Summary

Intuitively, it seems that leveraging native Azure VPN gateway services would be ideal. However, due to the limitations outlined in this article, administrators must decide carefully if any of these prevent adoption in their environment. Although not formally supported, many organizations deploy Windows Server Routing and Remote Access (RRAS) servers in Azure to address these limitations.

Additional Information

Always On VPN Options for Azure Deployments

Always On VPN with Azure Gateway

Always On VPN Device Tunnel with Azure VPN Gateway

Always On VPN and RRAS in Azure

What is Azure VPN Gateway?

What is Azure Virtual WAN?

Always On VPN Book Available for Pre-Order

Great news! My new book, Implementing Always On VPN, is now available for pre-order on Amazon.com. This new book, scheduled for release in late 2021, is a comprehensive implementation guide for Windows 10 Always On VPN. Drawing on many years of experience deploying Always On VPN for organizations worldwide, it covers all aspects of an Always On VPN deployment, including planning and design, prerequisite gathering, infrastructure preparation, and client deployment.

In addition, it contains detailed, prescriptive guidance for advanced configuration options such as application and traffic filtering and proxy server configuration. Cloud deployments using Azure VPN gateway and Virtual WAN are covered, and it includes guidance for configuring Azure MFA and Conditional Access.

Also, the book includes thorough guidance for provisioning certificates using Microsoft Endpoint Manager/Intune using both PKCS and SCEP. It outlines options for high availability for VPN and authentication infrastructure and provides details for ongoing system maintenance and operational support.

Finally, the book has an entire chapter dedicated to troubleshooting and resolving common (and not so common!) issues encountered with Windows 10 Always On VPN.

Reserve your copy today. Pre-order Implementing Always On VPN now!

Chapter List

  1. Always On VPN Overview
  2. Plan an Always On VPN Deployment
  3. Prepare the Infrastructure
  4. Configure Windows Server for Always On VPN
  5. Provision Always On VPN clients
  6. Advanced Configuration
  7. Cloud Deployments
  8. Deploy Certificates with Intune
  9. Integrating Azure MFA
  10. High Availability
  11. Monitor and Report
  12. Troubleshooting

Always On VPN IKEv2 Load Balancing and NAT

Always On VPN IKEv2 Load Balancing and NATOver the last few weeks, I’ve worked with numerous organizations and individuals troubleshooting connectivity and performance issues associated with Windows 10 Always On VPN, and specifically connections using the Internet Key Exchange version 2 (IKEv2) VPN protocol. An issue that appears with some regularity is when Windows 10 clients fail to connect with error 809. In this scenario, the server will accept connections without issue for a period of time and then suddenly stop accepting requests. When this happens, existing connections continue to work without issue in most cases. Frequently this occurs with Windows Server Routing and Remote Access Service (RRAS) servers configured in a clustered array behind an External Load Balancer (ELB).

Network Address Translation

It is not uncommon to use Network Address Translation (NAT) when configuring Always On VPN. In fact, for most deployments the public IP address for the VPN server resides not on the VPN server, but on an edge firewall or load balancer connected directly to the Internet. The firewall/load balancer is then configured to translate the destination address to the private IP address assigned to the VPN server in the perimeter/DMZ or the internal network. This is known a Destination NAT (DNAT). Using this configuration, the client’s original source IP address is left intact. This configuration presents no issues for Always On VPN.

Source Address Translation

When troubleshooting these issues, the common denominator seems to be the use of Full NAT, which includes translating the source address in addition to the destination. This results in VPN client requests arriving at the VPN server as appearing not to come from the client’s original IP address, but the IP address of the network device (firewall or load balancer) that is translating the request. Full NAT may be explicitly configured by an administrator, or in the case of many load balancers, configured implicitly because the load balancer is effectively proxying the connection.

Known Issues

IKEv2 VPN connections use IPsec for encryption, and by default, Windows limits the number of IPsec Security Associations (SAs) coming from a single IP address. When a NAT device is performing destination/full NAT, the VPN server sees all inbound IKEv2 VPN requests as coming from the same IP address. When this happens, clients connecting using IKEv2 may fail to connect, most commonly when the server is under moderate to heavy load.

Resolution

The way to resolve this issue is to ensure that any load balancers or NAT devices are not translating the source address but are performing destination NAT only. The following is configuration guidance for F5, Citrix ADC (formerly NetScaler), and Kemp load balancers.

F5

On the F5 BIG-IP load balancer, navigate to the Properties > Configuration page of the IKEv2 UDP 500 virtual server and choose None from the Source Address Translation drop-down list. Repeat this step for the IKEv2 UDP 4500 virtual server.

Always On VPN IKEv2 Load Balancing and NAT

Citrix ADC

On the Citrix ADC load balancer, navigate to System > Settings > Configure Modes and check the option to Use Subnet IP.

Always On VPN IKEv2 Load Balancing and NAT

Next, navigate to Traffic Management > Load Balancing > Service Groups and select the IKEv2 UDP 500 service group. In the Settings section click edit and select Use Client IP. Repeat these steps for the IKEv2 UDP 4500 service group.

Always On VPN IKEv2 Load Balancing and NAT

Kemp

On the Kemp LoadMaster load balancer, navigate to Virtual Services > View/Modify Services and click Modify on the IKEv2 UDP 500 virtual service. Expand Standard Options and select Transparency. Repeat this step for the IKEv2 UDP 4500 virtual service.

Always On VPN IKEv2 Load Balancing and NAT

Caveat

Making the changes above may introduce routing issues in your environment. When configuring these settings, it may be necessary to configure the VPN server’s default gateway to use the load balancer to ensure proper routing. If this is not possible, consider implementing the workaround below.

Workaround

To fully resolve this issue the above changes should be made to ensure the VPN server can see the client’s original source IP address. If that’s not possible for any reason, the following registry key can be configured to increase the number of established SAs from a single IP address. Be advised this is only a partial workaround and may not fully eliminate failed IKEv2 connections. There are other settings in Windows that can prevent multiple connections from a single IP address which are not adjustable at this time.

To implement this registry change, open an elevated PowerShell command window on the RRAS server and run the following commands. Repeat these commands on all RRAS servers in the organization.

New-ItemProperty -Path ‘HKLM:SYSTEM\CurrentControlSet\Services\IKEEXT\Parameters\’ -Name IkeNumEstablishedForInitialQuery -PropertyType DWORD -Value 50000 -Force

Restart-Service IKEEXT -Force -PassThru

Additional Information

IPsec Traffic May Be Blocked When A Computer is Behind a Load Balancer

Windows 10 Always On VPN IKEv2 Load Balancing with Citrix NetScaler ADC

Windows 10 Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Windows 10 Always On VPN IKEv2 Load Balancing with Kemp LoadMaster