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 Secure Boot UEFI Certificates Expiring June 2026

For IT administrators responsible for managing Windows devices, a crucial certificate update milestone is coming in June 2026 that could result in degraded security for systems that are not updated. Specifically, the Microsoft certificates that manage UEFI Secure Boot trust will expire, potentially allowing untrusted or malicious software to load on affected machines during system boot.

Secure Boot

Windows Secure Boot is a UEFI firmware security feature that ensures a computer boots only with trusted, digitally signed operating system loaders and drivers, preventing malicious code (such as rootkits or compromised bootloaders) from loading during startup. Introduced with Windows 8, it verifies the cryptographic signatures of boot components against a database of authorized keys, blocking unauthorized or tampered software to protect system integrity from the earliest stages of boot.

Chain of Trust

The UEFI Platform Key (PK) is the ultimate root of trust in Secure Boot. It is a single public key owned by the device manufacturer and stored in firmware. The PK certificate signs the Key Exchange Key (KEK) and grants authority to modify the other Secure Boot databases, such as the allowed database (DB) and the disallowed database (DBX). The DB and DBX contain certificates and signatures for authorized and unauthorized software, respectively.

Microsoft Secure Boot Certificate Expiration

Two crucial Microsoft Secure Boot certificates are set to expire in June 2026. They are:

  • Microsoft Corporation KEK CA 2011 (stored in KEK)
  • Microsoft UEFI CA 2011 (stored in DB)

In addition, another critical Microsoft Secure Boot certificate expires in October 2026.

  • Microsoft Windows Production PCA 2011 (stored in DB)

When these certificates expire, devices may fail to recognize trusted bootloaders, and future Secure Boot policies may not be applied. Updating the certificates ensures continued protection against malicious rootkits and ensures Windows firmware compliance

View Certificate Information

Ideally, administrators could use PowerShell to view these UEFI Secure Boot certificates. Sadly, the output of the Get-SecureBootUEFI PowerShell command is not particularly helpful and does not display any pertinent certificate details.

Get-SecureBootUEFI -Name KEK

PowerShell Script

To address this limitation, I’ve created a PowerShell script that allows administrators to view all UEFI certificates, including PK, KEK, and DB certificates, and optionally save them as base64-encoded files. The script is available on GitHub and in the PowerShell gallery.

Install-Script -Name Get-UEFICertificate -Scope CurrentUser

View UEFI Certificates

After downloading the Get-UEFICertificate PowerShell script, run the following command to view the KEK database.

Get-UEFICertificate -Type KEK

In this example, the only KEK certificate is the expiring Microsoft Corporation KEK CA 2011 certificate. Running the command and specifying the DB type shows only the expiring Microsoft Windows Product PCA 2011 certificate.

Note: UEFI also includes hashes of specific executables in the DB and DBX databases. By default, this script focuses on UEFI certificates and omits hash calculations for brevity. Use the -IncludeHashes switch to view this information.

Updating Microsoft UEFI Certificates

With the October 2025 updates, Microsoft introduced new registry keys to enable and monitor the update status of these UEFI Secure Boot certificates.

Status

To begin, administrators can check the status of the update process by reading the value of the UEFICA2023Status registry key.

Get-ItemProperty -Path HKLM:\SYSTEM\CurrentControlSet\Control\SecureBoot\Servicing\ -Name UEFICA2023Status | Select-Object UEFICA2023Status

Update

To initiate the update process, set the value of AvailableUpdates to 0x5944.

Set-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecureBoot’ -Name ‘AvailableUpdates’ -Value 0x5944

Next, start the Secure-Boot-Update scheduled task.

Start-ScheduledTask -TaskName ‘\Microsoft\Windows\PI\Secure-Boot-Update’

Once complete, the UEFICA2023Status indicates InProgress.

After a reboot, start the Secure-Boot-Update scheduled task once more. The UEFICA2023Status should indicate that it has been updated (may require one more reboot!).

Updated Certificates

After the update process completes, run the Get-UEFICertificate PowerShell script to confirm that new certificates have been added to UEFI Secure Boot.

Updated Microsoft KEK Certificates

Updated Microsoft DB Certificates

Summary

With multiple Microsoft Secure Boot CA certificates expiring in 2026, organizations need to ensure devices are updated to maintain a valid UEFI trust chain. This guide shows how to view existing firmware certificates, apply Microsoft’s Secure Boot CA 2023 updates, and confirm that new KEK and DB certificates have been installed. Completing this process now will ensure devices remain protected from tampered or malicious boot components as the 2026 expiration dates approach.

Additional Information

Windows Secure Boot certificate expiration and CA updates

Registry key updates for Secure Boot: Windows devices with IT-managed updates

Get-UEFICertificate PowerShell Script on GitHub

Get-UEFICertificate PowerShell Script in the PowerShell Gallery

What’s New in Absolute Secure Access v14

Absolute Software recently announced a significant upgrade for its popular secure remote access and Zero Trust Network Access (ZTNA) solution. Version 14 of Secure Access introduces many compelling new features and updates that administrators will find beneficial. In addition, crucial security vulnerabilities in the previous release have been addressed.

New Features

Absolute Secure Access v14.x includes many enhancements over previous releases. Here are a few of the highlights.

Improved Performance

Absolute Secure Access v14 provides much faster throughput on multi-gigabit networks (e.g., 2.5Gbps Wi-Fi 6E/7 or 10Gbps wired). New kernel-level optimizations reduce CPU overhead by up to 40% on high-speed links, improving performance on faster networks.

Modern Certificate Handling

SHA-1 has been deprecated since 2011, and beginning with Absolute Secure Access v14, support for SHA-1 certificates has been removed completely.

Enhanced Client Auto Reconnect

Improved client auto-reconnect logic now survives Windows standby mode for more than 12 hours (previous versions were capped at around 4 hours). This will reduce frustration when devices return from standby for extended periods.

Automatic Host Group Updates

Host groups are an excellent way to streamline policy configuration for services like Microsoft 365 and AWS. These cloud providers publish the IP addresses of their services, which are dynamic and often change over time. Absolute Secure Access v14 now supports automatic host group updates for these services. Microsoft 365 updates occur every 28 days, and AWS updates occur every 5 days by default. This interval is configurable for administrators.

Security Updates

Absolute Secure Access v14 closes four server-side CVEs as well as 14 third-party CVEs (Apache, OpenSSL, etc.) that were not patched in v13.x.

Summary

If you have deployed previous versions of Absolute Secure Access, consider upgrading to v14.x today. You’ll gain improved performance, reduced administrative overhead, critical security updates, and much more. If you’d like help with your migration or want to learn more about the new capabilities in Absolute Secure Access v14, fill out the form below, and I’ll provide more information.

Additional Information

Absolute Secure Access

Absolute Secure Access Enterprise VPN Advanced Features In Depth

Absolute Secure Access and IPv6