Always On VPN Options for Azure Deployments

Always On VPN Options for Azure DeploymentsOrganizations everywhere are rapidly adopting Microsoft Azure public cloud infrastructure to extend or replace their existing datacenter. As traditional on-premises workloads are migrated to the cloud, customers are looking for options to host VPN services there as well.

Windows Server

Windows Server with the Routing and Remote Access Service (RRAS) installed is a popular choice for on-premises Always On VPN deployments. Intuitively it would make sense to deploy Windows Server and RRAS in Azure as well. However, at the time of this writing, RRAS is not a supported workload on Windows Server in Azure.

Always On VPN Options for Azure Deployments

Reference: https://support.microsoft.com/en-us/help/2721672/microsoft-server-software-support-for-microsoft-azure-virtual-machines/

Although explicitly unsupported, it is possible to deploy Windows Server and RRAS in Azure for Always On VPN. In my experience it works well and can be an option for organizations willing to forgo formal support by Microsoft.

Azure Gateway

Options for supporting Always On VPN connections using native Azure VPN infrastructure depend on the type of VPN gateway chosen.

VPN Gateway

The Azure VPN Gateway can be configured to support client-based (point-to-site) VPN. With some additional configuration it can be used to support Windows 10 Always On VPN deployments. Azure VPN gateway supports either IKEv2 or SSTP VPN protocols for client connections. The Azure VPN gateway has some limitations though. Consider the following:

  • A route-based VPN gateway is required
  • A maximum of 1000 concurrent IKEv2 connections are supported when using the VpnGw3 or VpnGw3AZ SKUs (2000 supported in active/active mode)
  • A maximum of 128 concurrent SSTP connections are supported on all gateway SKUs (256 supported in active/active mode)
  • The gateway can be configured to support either device or user connections, not both.

Virtual WAN

Azure Virtual WAN is the future of remote connectivity for Azure. It includes support for client-based VPN (currently in public preview at the time of this writing), but only supports IKEv2 and OpenVPN VPN protocols for client connections. SSTP is not supported at all. Further, OpenVPN is not supported for Windows 10 Always On VPN, leaving IKEv2 as the only option, which poses some potential operational challenges. Virtual WAN offer much better scalability though, supporting up to 10,000 concurrent client-based VPN connections. Like the Azure VPN gateway, Azure Virtual WAN can be configured to support either device or user connections, not both.

Virtual Appliance

The most supportable option for hosting VPN services in Azure for Windows 10 Always On VPN is to deploy a third-party Network Virtual Appliance (NVA). They are available from a variety of vendors including Cisco, Check Point, Palo Alto Networks, Fortinet, and many others. To support Windows 10 Always On VPN, the NVA vendor must either support IKEv2 for client-based VPN connections or have a Universal Windows Platform (UWP) VPN plug-in client available from the Microsoft store. Click here to learn more about Always On VPN and third-party VPN devices.

Note: Be careful when choosing an NVA as some vendors support IKEv2 only for site-to-site VPN, but not client-based VPN!

Hybrid Deployments

For organizations with hybrid cloud deployments (infrastructure hosted on-premises and in Azure), there are several options for choosing the best location to deploy VPN services. In general, it is recommended that client VPN connections be established nearest the resources accessed by remote clients. However, having VPN servers hosted both on-premises and in Azure is fully supported. In this scenario Azure Traffic Manager can be configured to intelligently route VPN connections for remote clients.

NetMotion Mobility

The NetMotion Mobility purpose-built enterprise VPN is a popular replacement for Microsoft DirectAccess. It is also an excellent alternative for enterprise organizations considering a migration to Always On VPN. It is a software-based solution that can be deployed on Windows Server and is fully supported running in Microsoft Azure. It offers many advanced features and capabilities not included in other remote access solutions.

Summary

Administrators have many options for deploying VPN servers in Azure to support Windows 10 Always On VPN. Windows Server and RRAS is the simplest and most cost-effective option, but it is not formally supported by Microsoft. Azure VPN gateway is an interesting alternative but lacks enough capacity for larger deployments. Azure Virtual WAN is another option but has limited protocol support. Deploying an NVA is a good choice, and NetMotion Mobility is an excellent alternative to both DirectAccess and Always On VPN that is software-based and fully supported in Azure.

Additional Information

Windows 10 Always On VPN with Azure Gateway

Windows 10 Always On VPN and Third-Party VPN Devices

Windows 10 Always On VPN and Windows Server Routing and Remote Access Service (RRAS)

Windows 10 Always On VPN IKEv2 Features and Limitations

Windows 10 Always On VPN Multisite with Azure Traffic Manager

Comparing DirectAccess and NetMotion Mobility

Deploying NetMotion Mobility in Microsoft Azure

Always On VPN SSTP Load Balancing with F5 BIG-IP

Always On VPN SSTP Load Balancing with F5 BIG-IP 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.

Load Balancing SSTP

In a recent post, I described some of the use cases and benefits of SSTP load balancing as well as the offloading of TLS for SSTP VPN connections. Using a load balancer for SSTP VPN connections increases scalability, and offloading TLS for SSTP reduces resource utilization and improves performance for VPN connections. There are positive security benefits too.

Configuration

Enabling load balancing for SSTP on the F5 BIG-IP load balancer is fundamentally similar to load balancing HTTPS web servers. However, there are a few subtle but important differences.

Default Monitor

The default HTTP and HTTPS monitors on the F5 will not accurately reflect the health of the SSTP service running on the RRAS server. In addition, using a simple TCP port monitor could yield unexpected results. To ensure accurate service status monitoring, a new custom monitor must be created to validate the health of the SSTP service.

Custom SSTP Monitor

Open the F5 BIG-IP management console and follow the steps below to create and assign a new custom monitor for SSTP.

Create Monitor

1. In the navigation tree highlight Local Traffic.
2. Click Monitors.
3. Click Create.

Always On VPN SSTP Load Balancing with F5 BIG-IP

4. Enter a descriptive name in the Name field and from the Type drop-down list choose HTTP if TLS offload is enabled, or HTTPS if it is not.
5. In the Send String field enter HEAD /sra_{BA195980-CD49-458b-9E23-C84EE0ADCD75}/ HTTP/1.1\r\nHost:r\nConnection: Close\r\n\r\n.
6. In the Receive String field enter HTTP/1.1 401.
7. Click Finished.

Always On VPN SSTP Load Balancing with F5 BIG-IP

Assign Monitor

1. Below Local Traffic click Pools.
2. Click on the SSTP VPN server pool.
3. In the Health Monitors section select the SSTP VPN health monitor from the Available list and make it Active.
4. Click Update.

Always On VPN SSTP Load Balancing with F5 BIG-IP

CLI Configuration

If you prefer to configure the SSTP VPN monitor using the F5’s Command Line Interface (CLI), you can download the monitor configuration from my GitHub here.

TLS Offload

It is generally recommended that TLS offload not be enabled for SSTP VPN. However, if TLS offload is desired, it is configured in much the same way as a common HTTPS web server. Specific guidance for enabling TLS offload on the F5 BIG-IP can be found here. Details for configuring RRAS and SSTP to support TLS offload can be found here.

Certificates

When enabling TLS offload for SSTP VPN connections it is recommended that the public SSL certificate be installed on the RRAS server, even though TLS processing will be handled on the F5 and HTTP will be used between the F5 and the RRAS server. If installing the public SSL certificate on the RRAS server is not an option, additional configuration will be required. Specifically, TLS offload for SSTP must be configured using the Enable-SSTPOffload PowerShell script, which can be found here.

Once the script has been downloaded, open an elevated PowerShell command window and enter the following command.

Enable-SSTPOffload -CertificateHash [SHA256 Certificate Hash of Public SSL Certificate] -Restart

Example:

Enable-SSTPOffload -CertificateHash “C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2” -Restart

Re-Encryption

When offloading TLS for SSTP VPN connections, all traffic between the F5 and the RRAS server will be sent in the clear using HTTP. In some instances, TLS offload is required only for traffic inspection, not performance gain. In this scenario the F5 will be configured to terminate and then re-encrypt connections to the RRAS server. When terminating TLS on the F5 and re-encrypting connections to the RRAS server is required, the same certificate must be used on both the F5 and the RRAS server. Using different certificates on the RRAS server and the load balancer is not supported.

Additional Information

Windows 10 Always On VPN SSTP Load Balancing and SSL Offload

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN ECDSA SSL Certificate Request for SSTP

Windows 10 Always On VPN SSTP Connects then Disconnects

Windows 10 Always On VPN Load Balancing Deployment Guide for Kemp Load Balancers

 

Always On VPN IKEv2 Features and Limitations

Always On VPN IKEv2 Features and LimitationsThe Internet Key Exchange version 2 (IKEv2) VPN protocol is a popular choice for Windows 10 Always On VPN deployments. IKEv2 is a standards-based IPsec VPN protocol with customizable security parameters that allows administrators to provide the highest level of protection for remote clients. In addition, it provides important interoperability with a variety of VPN devices, including Microsoft Windows Server Routing and Remote Access Service (RRAS) and non-Microsoft platforms such as Cisco, Checkpoint, Palo Alto, and others.

IKEv2 Limitations

IKEv2 is clearly the protocol of choice in terms of security. It supports modern cryptography and is highly resistant to interception. It’s not without some operational challenges, however. Consider the following.

Firewalls

IKEv2 uses UDP ports 500 and 4500 for communication. Unfortunately, these ports are not always open. Often, they are blocked by network administrators to prevent users from bypassing security controls or attackers from exfiltrating data.

Fragmentation

IKEv2 packets can become quite large at times, especially when using client certificate authentication with the Protected Extensible Authentication Protocol (PEAP). This can result in fragmentation occurring at the network layer. Unfortunately, many firewalls and network devices are configured to block IP fragments by default. This can result in failed connection attempts from some locations but not others.

Load Balancing

Load balancing IKEv2 connections is not entirely straightforward. Without special configuration, load balancers can cause intermittent connectivity issues for Always On VPN connections. Guidance for configuring IKEv2 load balancing on the Kemp LoadMaster and the F5 BIG-IP can be found here:

IKEv2 Fragmentation

IKEv2 fragmentation can be enabled to avoid IP fragmentation and restore reliable connectivity. IKEv2 fragmentation is supported in Windows 10 and Windows Server beginning with v1803. Guidance for enabling IKEv2 fragmentation on Windows Server RRAS can be found here. Support for IKEv2 fragmentation on non-Microsoft firewall/VPN devices is vendor-specific. Consult with your device manufacturer for more information.

IKEv2 Security and RRAS

Be advised that the default security settings for IKEv2 on Windows Server RRAS are very poor. The minimum recommended security settings and guidelines for implementing them can be found here.

IKEv2 or TLS?

IKEv2 is recommend for deployments where the highest level of security and protection is required for remote connections. In these scenarios, the sacrifice of ubiquitous availability in favor of ultimate security might be desired.

SSTP or another TLS-based VPN protocol is recommended if reliable operation and connectivity are desired. SSTP and TLS VPNs can be configured to provide very good security by following the security and implementation guidelines found here.

IKEv2 with TLS Fallback

In theory, preferring IKEv2 and falling back to the Secure Socket Tunneling Protocol (SSTP) or another TLS-based VPN protocol when IKEv2 is unavailable would seem like a logical choice. This would ensure the highest level of protection, while still providing reliable connectivity. Unfortunately, the Windows VPN client doesn’t work this way in practice. Details here.

Additional Information

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

Windows 10 Always On VPN IKEv2 Load Balancing with Kemp LoadMaster

Windows 10 Always On VPN IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 and SSTP Fallback

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN Protocol Recommendations for Windows Server RRAS