All posts in category end of life

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

Windows Server 2016 End of Life January 2027: Plan Your AD CS Migration Now

Happy New Year, everyone! As the calendar rolls over to 2026, it’s time to start planning the migration of workloads hosted on Windows Server 2016. Mainstream support ended for Windows Server 2016 on January 11, 2022, after which it entered extended support. However, extended support for Windows Server 2016 ends on January 12, 2027, at which point it will be end of life and no longer supported. Running production workloads on Windows Server 2016 beyond this date exposes organizations to significant security risk, as it no longer receives security updates, leaving these systems vulnerable to exploits.

Active Directory Certificate Services

Many organizations are still running critical infrastructure on Windows Server 2016. Administrators often delay upgrading Microsoft Active Directory Certificate Services (AD CS) due to its complexity. However, a well-planned AD CS migration not only reduces risk but also provides an opportunity to modernize cryptography, certificate templates, and operational practices.

Certificate Authorities

Administrators must carefully migrate Certificate Authorities (CAs) running on Windows Server 2016 to minimize downtime. In environments where ongoing CA maintenance has been limited, migrating the CA database can be especially challenging. If the CA is installed on a domain controller, now is a good time to consider separating these services to ensure reliable operation. Also, it’s a good idea to evaluate the CA’s configuration and security posture during migration to enhance security and improve service resilience.

NDES Servers

Microsoft Network Device Enrollment Services (NDES) servers, commonly deployed to facilitate certificate enrollment via Microsoft Intune, pose a unique challenge during migration. Unfortunately, configuring NDES is exceedingly complex and error-prone. NDES relies on a delicate combination of specialized IIS configuration, AD service accounts, custom certificate templates, and CA permissions, making even minor changes risky without proper planning. Not surprisingly, administrators are often hesitant to touch these systems as they are notoriously difficult to troubleshoot when problems arise.

Pro Tip: We spend an entire day covering NDES configuration in the Mastering Enterprise PKI Certificates with Microsoft Intune training course. The next session is March 10-12, 2026. Register now!

Intune Certificate Connectors

Don’t overlook Windows Server 2016 servers with the Intune Certificate Connector installed. Fortunately, this is one of the more manageable workloads to migrate. All that’s required is to install new connectors on supported servers and delete the old ones.

Summary

With extended support for Windows Server 2016 ending on January 12, 2027, organizations running production workloads—especially critical infrastructure such as Active Directory Certificate Services (AD CS), Certificate Authorities (CAs), and NDES servers—face significant security risks from unpatched vulnerabilities once the OS reaches end-of-life. Careful migration planning to newer versions such as Windows Server 2022 or 2025 is essential to minimize downtime, improve security posture, and ensure long-term resilience.

Start Planning Now

Don’t leave these mission-critical infrastructure services to the last minute! Begin planning your migration today. If you’d like expert guidance, I have many years of experience migrating these workloads. I have developed specialized tools and techniques to ensure a smooth, secure, and successful transition. Fill out the form below to schedule a free one-hour consultation to assess your Windows Server 2016 AD CS workloads, identify migration risks, and outline next steps.

Additional Information

Windows Server 2016 Lifecycle Policy

PKI Fundamentals with Microsoft Active Directory Certificate Services (AD CS) Online Training Course

Mastering Enterprise PKI Certificates with Microsoft Intune Online Training Course

PowerON Platforms are No More

If you’re a follower of this website, you are undoubtedly familiar with PowerON Platforms as I have promoted their products extensively over the years. Dynamic Profile Configurator (DPC) is a clever solution that enables Always On VPN client configuration provisioning and management using Active Directory group policy. They recently introduced a cloud-based centralized reporting solution for organizations with multiple VPN servers. I worked closely with PowerON and influenced many of the features of these great technologies.

Out of Business

Sadly, I learned recently that PowerON Platforms has entered insolvency. Effective October 16, 2024, PowerON Platforms now cease to exist. If you are a current customer of theirs, you likely have received a notification email already.

The Future

Many of my customers have asked what will become of DPC and their cloud-based reporting solution. Here is some additional information.

DPC

Fortunately, DPC will live on through open source. My good friend and primary developer of DPC, Leo D’Arcy, is currently working on refactoring the software to meet open-source specifications. Although I don’t have a timeline for when the software will be available for download, I hope it will be soon.

You can follow the GitHub repository for the open-source DPC here.

If you have a current DPC license, the product should continue to work without issue. You can upgrade to the open-source version of DPC in the future if you choose to. You will likely encounter problems if you use DPC with a trial license. If this happens, contact me directly, and I’ll assist you.

Reporting

The PowerON Platforms Always On VPN reporting solution is dead and will not continue. If you were using this product, I would suggest deleting the resource group you created in Azure for this and the PowerBI application installed for it.

In addition, Always On VPN administrators should remove the reporting agent software from their VPN servers. You can do this on GUI installations using the Add or Remove Programs control panel app.

If you’ve installed the reporting agent on Server Core systems, you can remove it by running the following PowerShell command.

Get-WmiObject -Class Win32_Product | Where-Object {$_.IdentifyingNumber -Match ‘{FFFC6424-82BB-49C5-9112-2C1436717C9C}’ } | Invoke-WmiMethod -Name Uninstall

Support

With PowerON Platforms out of business, their products are no longer supported. However, if you have issues with DPC or have any questions, please don’t hesitate to contact me. I’ll provide as much support as I can.

Additional Information

Always On VPN Dynamic Profile Configurator (DPC) Open Source on GitHub

2 Comments

by Richard M. Hicks on October 29, 2024 • Permalink

Tagged Always On VPN, AOVPN, DPC, Dynamic Profile Configurator, GitHub, MDM, Microsoft, open source, PowerON, PowerON Platforms, VPN, Windows, Windows 10, Windows 11

Posted by Richard M. Hicks on October 29, 2024

https://directaccess.richardhicks.com/2024/10/29/poweron-platforms-are-no-more/

Richard M. Hicks Consulting, Inc.

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All posts in category end of life

Always On VPN and Azure VPN Gateway SSTP Protocol Retirement