Always On VPN and Azure VPN Gateway SSTP Protocol Retirement

The Azure VPN gateway has been an option for supporting Microsoft Always On VPN client connections for organizations moving resources to the cloud. Today, Azure VPN gateway supports Internet Key Exchange version 2 (IKEv2), OpenVPN, and Secure Socket Tunneling Protocol (SSTP), although SSTP support has long been limited in scope and scalability. However, Microsoft recently indicated that some important changes are coming soon that will affect VPN protocol support on the Azure VPN gateway.

SSTP and Azure VPN Gateway

Microsoft has announced plans to deprecate and eventually remove support for SSTP on the Azure VPN gateway.

Key Dates

Here is Microsoft’s timeline for retiring SSTP for VPN connections.

  • March 31, 2026 – SSTP can no longer be enabled on new or existing gateways
  • March 31, 2027 – Existing SSTP connections will stop functioning

SSTP: Second Class Citizen

The retirement of SSTP for Azure VPN gateway should not have a significant impact on Always On VPN deployments. Support for SSTP on Azure VPN gateway has always been limited, making it a less viable option for most Always On VPN deployments. SSTP connections are capped at 128 concurrent connections (256 in active-active mode), regardless of gateway SKU. Additionally, Azure VPN gateway does not support simultaneous user and device tunnels, further limiting its usefulness in modern Always On VPN designs.

Plan Migration Now

If you are using Azure VPN gateway to support Always On VPN client connections, now is the time to begin planning a migration to IKEv2, which offers better scalability and native Always On VPN support. Alternatively, consider Windows Server RRAS in Azure, a third-party VPN solution, or Entra Private Access if Azure VPN gateway no longer meets your requirements.

More Information

For official guidance, see SSTP Protocol Retirement and Connections Migration. If you’re unsure how this change affects your Always On VPN deployment, or you would like help planning a migration, this is a good time to review your design and roadmap. Fill out the form below, and I’ll provide you with more information.

Additional Information

SSTP Protocol Retirement and Connections Migration

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

Windows Server RRAS in Microsoft Azure

Microsoft Entra Private Access

Always On VPN RRAS and PowerShell 7

PowerShell is an essential tool for administrators supporting Microsoft Always On VPN. It is critical for configuring supporting infrastructure services, such as Routing and Remote Access (RRAS) and Network Policy Server (NPS), as well as provisioning and managing Always On VPN client configuration settings on endpoints. The current version of PowerShell, PowerShell 7.5.3, is a game-changer for scripting and automation, bringing a host of improvements over its predecessors. PowerShell 7 offers better performance, lower memory usage, and cross-platform support (Windows, macOS, and Linux), making it more versatile than ever.

Problem in PowerShell 7

Recently, I discovered an oddity with PowerShell 7 when reviewing the configuration of an RRAS server. Specifically, PowerShell 7 differs in the way it produces output for the Get-RemoteAccess command, preventing administrators from viewing the details of the currently configured TLS certificate used for SSTP VPN connections in RRAS.

PowerShell 5

Running Get-RemoteAccess in PowerShell 5 provides detailed information about the SslCertificate property in the output of the command, as shown here.

Note that the data returned in the SslCertificate property is of the type X509Certificate2.

PowerShell 7

In PowerShell 7, Get-RemoteAccess displays only a string of numbers instead of detailed certificate information.

Notably, the data returned in the SslCertificate property is of the type System.Byte.

Solution

While PowerShell 7 doesn’t output the certificate details in human-readable form, you can easily convert the data using the following PowerShell command.

[System.Security.Cryptography.X509Certificates.X509Certificate2]::new((Get-RemoteAccess).SslCertificate) | Format-List

AovpnTools Module

To simplify administration, I’ve added a function to my AovpnTools PowerShell module called Get-VpnServerTlsCertificate. This function allows you to view the currently configured SSTP certificate details directly with a single command. In addition, you have the option to save the certificate to a file for further inspection and troubleshooting.

The GetVpnServerTlsCertificate function is included in AovpnTools v1.9.8 and later. You can install AovpnTools from the PowerShell gallery by running the following command.

Install-Module -Name AovpnTools

You can also find the AovpnTools PowerShell module on GitHub.

Summary

With PowerShell 7, RRAS certificate details display differently, but administrators can quickly resolve this using a simple conversion or the Get-VpnServerTlsCertificate function in the AovpnTools module. Either way, administrators can continue to use PowerShell 7 to manage their Windows Server RRAS servers.

Additional Information

Installing PowerShell 7 on Windows

AovpnTools in the PowerShell Gallery

AovpnTools on GitHub

Microsoft Deprecates Legacy VPN Protocols

It’s long overdue, but Microsoft has finally announced the formal deprecation of the Point-to-Point Tunnel Protocol (PPTP) and the Layer 2 Tunneling Protocol (L2TP) in Windows Server Routing and Remote Access (RRAS) Servers. Both protocols have long since been replaced with more secure alternatives such as the Secure Socket Tunneling Protocol (SSTP) and Internet Key Exchange version 2 (IKEV2). However, many organizations have RRAS servers configured using these legacy protocols to support ad-hoc, on-demand access for non-managed users and devices.

Deprecated Protocols

There are a few reasons why Microsoft has deprecated these legacy protocols. Consider the following.

PPTP

It’s been widely known for many years that PPTP is broken and terribly insecure. Using this VPN protocol today is tremendously risky.

L2TP

L2TP is still considered secure, for the most part. However, it has been replaced with IKEv2, which is more secure and efficient.

Future Support

Although Microsoft made the announcement recently, the protocols will still be included in Windows Server 2025 when released later this year. However, Microsoft may remove these protocols from future Windows Server releases.

Always On VPN

Those who have deployed Microsoft Always On VPN are likely already using modern, secure VPN protocols, so this deprecation announcement won’t impact them. Although PPTP and L2TP are technically supported with Always On VPN, they are not commonly configured.

Recommendations

Administrators using Windows Server RRAS for VPN access using PPTP are encouraged to migrate to another protocol immediately. Those continuing to use L2TP should consider migrating soon.

Additional Information

Always On VPN Protocol Recommendations for Windows Server RRAS