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

Intune SCEP Profile Changes for Public S/MIME Certificates

Recently, the CA/Browser Forum, which is a voluntary consortium made up of public CAs, browser vendors, and other industry stakeholders, introduced new requirements for S/MIME certificates issued by public certification authorities (CAs). For organizations using Microsoft Intune SCEP device configuration profiles to enroll for these certificates, administrators must update Intune settings to ensure uninterrupted enrollment once the changes take effect.

Subject Name Changes

Beginning July 16, 2025, all public CAs will enforce these new S/MIME Baseline Requirements, mandating “Given Name” and “Surname” attributes in the Subject Name field of S/MIME certificates. By default, Intune user certificate profiles include only the “UserName” attribute in the Subject Name field.

Intune Support

Intune recently completed the rollout of these new attributes in SCEP profiles. Administrators can now update their SCEP profiles for third-party public CAs to include these new attributes for S/MIME certificates using the following supported variables.

G={{GivenName}}
SN={{SurName}}

To align with current public CA standards, include these two fields along with any other information required in the Subject name format field. Multiple values must be separated by commas without spaces, as shown in the example below.

Private CAs

Private CAs, like Active Directory Certificate Services (AD CS) or Intune Cloud PKI, are unaffected. If you are enrolling for S/MIME certificates using these services, no changes are required.

Reenrollment

It’s important to note that modifying an existing Intune SCEP profile will trigger certificate reissuance for all users and devices within the policy’s scope, which could yield unexpected results. When making changes to Intune certificate policies, it is best to create a new policy to supersede the old one, allowing administrators to pilot the new policy before its broad deployment.

Additional Information

CA/Browser Forum S/MIME Baseline Requirements

Mastering Certificates with Microsoft Intune Training August 2025

Strong Certificate Mapping for Intune PKCS and SCEP Certificates

The Case for Short-Lived Certificates in Enterprise Environments

Always On VPN SSTP and 47-Day TLS Certificates