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

Windows Server DHCP and Option 108

While enterprise adoption of IPv6 has been slow, it is still moving forward. For example, the U.S. federal government has mandated [M-21-07 – PDF] the transition to IPv6 to modernize its networks and enhance security, scalability, and interoperability. During the migration to IPv6, most systems will be configured with both IPv4 and IPv6, a configuration referred to as dual stack. Ultimately, the goal is the elimination of IPv4 entirely and the use of IPv6 exclusively. However, IPv6-only presents some unique challenges.

Access to IPv4

Although an organization can successfully migrate to IPv6-only networks internally, they do not control networks outside its boundaries. In some cases, a host on an IPv6-only network may need to communicate with an IPv4 resource. Administrators must deploy an IPv6 transition technology to support this scenario.

464XLAT

464XLAT, defined in RFC 6877, is a network architecture that facilitates the transition from IPv4 to IPv6 by enabling IPv4 traffic to operate over an IPv6-only network. It combines two translation mechanisms: a client-side translator (CLAT) on the user device, which converts IPv4 packets to IPv6, and a provider-side translator (PLAT) at the network edge, which converts the IPv6 packets back to IPv4 to communicate with IPv4-only internet services. This dual-translation approach allows devices in an IPv6-only environment to access both IPv6 and IPv4 resources without requiring a full IPv4 stack, making it an efficient solution for networks transitioning to IPv6 while maintaining compatibility with legacy IPv4 systems. To support 464XLAT, Windows provides specific functionality for CLAT, though with some limitations.

CLAT for Windows

Windows currently provides CLAT support only for cellular network interfaces. CLAT is not available for Wi-Fi or Ethernet interfaces today. However, Microsoft has publicly announced plans to extend CLAT support in Windows for these non-cellular network interfaces soon.

IPv6 Mostly

IPv6 Mostly, defined in RFC 8925, refers to a network configuration where IPv6 is the primary protocol for communication, but IPv4 is still supported for specific use cases. Devices in these networks prefer IPv6 for most operations, leveraging its larger address space and modern features, while maintaining limited IPv4 compatibility. IPv6 Mostly networks ease the transition from IPv4 to IPv6, balancing modern protocol adoption with support for older applications. They optimize resource usage and prepare networks for a future where IPv6 dominates, with tools like 464XLAT providing seamless IPv4 access when necessary.

DHCP Option 108

DHCP Option 108 is a specific configuration in DHCP that enables IPv6-only networks to signal clients to disable IPv4. When a client receives this option, it deactivates its IPv4 stack, relying solely on IPv6 for communication. Turning off IPv4 when it isn’t needed helps streamline network operations in IPv6-focused environments.

Option 108 and Windows Server DHCP

Commercial DHCP appliances like Infoblox and many open source DHCP platforms natively support DHCP option 108. However, no supported version of Windows Server, including the latest release (Windows Server 2025), supports DHCP option 108 natively. To enable DHCP option 108 on Windows DHCP servers, administrators can create a custom predefined option.

Custom Predefined Option

To create a custom predefined option for DHCP option 108 on a Windows DHCP server, open the DHCP management console (dhcpmgmt.msc) and perform the following steps.

  1. Right-click IPv4 and choose Set Predefined Options.
  2. Click Add.
  3. Enter IPv6 Only Preferred in the Name field.
  4. Select Long from the Data type drop-down list.
  5. Enter 108 in the Code field.
  6. Click Ok.

Assigning DHCP Option 108

Once complete, perform the following steps to assign DHCP option 108 to a DHCP scope.

  1. Select an IPv4 DHCP scope.
  2. Right-click Scope Options and choose Configure Options.
  3. Select 108 IPv6 Only Preferred from the Available Options list.
  4. Enter a value in seconds, in hexadecimal format. This value represents the duration for which a client should prefer IPv6-only mode. For example, 86,400 seconds (1 day) is 0x15180.
  5. Click Ok.

PowerShell

Custom predefined options can also be configured using PowerShell.

Custom Predefined Option

To create a custom predefined option for DHCP option 108, open an elevated PowerShell command on a Windows DHCP server and run the following command.

Add-DhcpServerv4OptionDefinition -Name ‘IPv6 Only Preferred’ -OptionId 108 -Type DWORD -PassThru

Assigning DHCP Option 108

To assign the custom predefined DHCP option 108 to a DHCP scope, run the following PowerShell command.

Set-DhcpServerv4OptionValue -ScopeId 172.16.5.0 -OptionId 108 -Value 0x15180 -PassThru

DHCP Offer

Once configured, if the client indicates support for DHCP option 108 in its DHCP Request, the DHCP server will include it in the DHCP Offer, as shown here.

Learn More

If you are interested in learning more about IPv6 Mostly and DHCP option 108, be sure to listen to the following episodes of the IPv6 Buzz Podcast.

Summary

As organizations continue their transition toward IPv6, DHCP option 108 provides administrators with a simple and effective way to reduce reliance on legacy IPv4 by signaling clients to prefer IPv6-only operation if they can support it. While Windows Server does not natively support this option, creating a custom predefined setting ensures administrators can take advantage of this important feature.

Additional Information

M-21-07 – Completing the Transition to IPv6 for U.S. Federal Government Agencies [PDF]

Microsoft Plans to Extend CLAT Support in Windows 11

RFC 6877 – 464XLAT: Combination of Stateful and Stateless Translation

RFC 8925 – IPv6-Only Preferred Option for DHCPv4

IPv6 Buzz Podcast on PacketPushers.Net

10 PowerShell Commands Always On VPN Administrators Should Know

Managing a secure and reliable VPN infrastructure is critical for supporting today’s highly mobile workforce. For Always On VPN administrators, PowerShell is an indispensable tool for achieving this goal. Not only can PowerShell be used to automate the installation and configuration of Windows Server Routing and Remote Access Service (RRAS) server, but it can also be used to audit configuration and monitor system health and user activity as well. In addition, it is highly recommended that the RRAS role be installed on Server Core for optimum security and performance. Administrators must be familiar with these PowerShell commands and more to support RRAS on Windows Server Core in their environment.

RemoteAccess Module

The RemoteAccess PowerShell module should be installed when the RRAS server is configured. There are 122 commands in this module, but only a subset of those pertain to the VPN server role. Here are ten popular commands for monitoring and managing an Always On VPN RRAS server.

Configuration Review

The following PowerShell commands are useful for reviewing the current RRAS server configuration.

Get-RemoteAccess – Displays the current configuration of the VPN server. Details include installation status, TLS certificate configuration, VPN client IP address assignment method, IPv4 and IPv6 addressing information (if using the static address assignment method), authentication type, and configured RADIUS servers.

Get-VpnAuthProtocol – Displays authentication configuration details such as accepted authentication types for both user and device connections, root certification authority (CA) certificate restrictions (if enabled), and certificate advertisement and EKU restrictions if enabled.

Get-VpnServerConfiguration – Displays additional VPN server configuration information, such as the IPsec configuration for IKEv2, the number of VPN ports configured, and more.

System Health

Get-RemoteAccessHealth – Displays the current health status of various VPN server services. The command’s default output is a little noisy. I recommend filtering it as follows:

Get-RemoteAccessHealth | Where-Object HealthState -NotMatch Disabled | Format-Table -AutoSize

User Activity

The following PowerShell commands can be used to view current and historical user activity details.

Get-RemoteAccessConnectionStatistics – Displays all active VPN connections on the server.

Get-RemoteAccessConnectionStatisticsSummary – Displays cumulative information about VPN connections on the server since the last service restart or reboot, such as the total number of connections, the number of unique users, the maximum number of concurrent connections, and the amount of data transferred.

Get-RemoteAccessUserActivity – Displays all active VPN connections for a specific user or device.

Management

The following PowerShell commands are helpful for reviewing authentication and logging settings.

Get-RemoteAccessRadius – Allows the administrator to view the currently configured RADIUS servers on the VPN server.

Get-RemoteAccessAccounting – Allows the administrator to view the current accounting repository (RADIUS or inbox) on the VPN server.

Clear-RemoteAccessInboxAccountingStore – Allows the administrator to remove log data from the Inbox Accounting database. Removing log data from the database can be helpful when transitioning a test server to production or to free up disk space by reducing the size of the logging database.

Additional Modules

In addition to the PowerShell commands above, Always On VPN administrators can leverage my custom PowerShell modules for advanced server and client configuration. These modules are published in the PowerShell Gallery.

AovpnTools – PowerShell module to configure and optimize Windows RRAS servers to support Always On VPN.

Install-Module -Name AovpnTools

InboxAccountingDatabaseManagement – PowerShell module to configure and manage the Inbox Accounting database for logging system information and user activity on the VPN server.

Install-Module -Name InboxAccountingDatabaseManagement

Additional Information

Always On VPN and RRAS on Windows Server Core

Inbox Accounting Database Management

AovpnTools PowerShell Module on GitHub

Inbox Accounting Database Module on GitHub