90 DAYS LEFT: Windows Server 2016 End of Life January 2027 – Plan Your AD CS Migration Now

Heads up, fellow Windows Server administrators! There are now just THREE MONTHS remaining before Windows Server 2016 reaches end of support, so now is the time to finalize any migrations for workloads hosted on this platform. Mainstream support ended on January 11, 2022, and Windows Server 2016 has since remained in extended support. However, extended support ends on January 12, 2027. After that date, Microsoft will no longer provide security updates or technical support, increasing the risk of running production workloads due to exposure to newly discovered vulnerabilities and 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 February 3-5, 2027. 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 risk running unsupported workloads in 2027! Complete 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

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

With just over six months remaining before Windows Server 2016 reaches end of support, now is the time to begin planning migrations for workloads hosted on this platform. Mainstream support ended on January 11, 2022, and Windows Server 2016 has since remained in extended support. However, extended support ends on January 12, 2027. After that date, Microsoft will no longer provide security updates or technical support, increasing the risk of running production workloads due to exposure to newly discovered vulnerabilities and 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 September 1-3, 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 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

Resolving PKCS Certificate Mapping Issues in Windows Autopilot Hybrid Join Deployments

Microsoft Windows Autopilot streamlines device provisioning through Intune, allowing IT administrators to preconfigure new Windows devices with minimal hands-on effort. However, when combined with Hybrid Entra Join and PKCS certificate deployment, specific challenges arise—particularly with certificate mapping and authentication.

Hybrid Entra Join

During autopilot provisioning, administrators may also choose to join the device to their on-premises Active Directory domain, a deployment model called Hybrid Entra join. Hybrid Entra join presents some unique challenges when using Autopilot to remotely provision devices. Specifically, the user must have connectivity to a domain controller to perform the first logon, as they do not have a user profile on the endpoint.

Device Tunnel

To support offline Hybrid Entra join during Autopilot provisioning, administrators can deploy the Always On VPN device tunnel to provide pre-logon connectivity to domain controllers. A device tunnel connection enables users to log on to their newly provisioned device remotely.

Requirements

The following prerequisites must be met to support the Always On VPN device tunnel.

  • The endpoint must be running Windows Enterprise edition.
  • An Always On VPN device tunnel profile must be assigned to the device.
  • A machine certificate must be deployed to the endpoint that includes the Client Authentication EKU (OID 1.3.6.1.5.5.7.3.2).

Note: If you plan to use the subscription step-up upgrade from Windows Professional to Windows Enterprise, the device tunnel will not connect automatically after provisioning is complete, which prevents the user from logging in. More details and a workaround for this issue can be found here.

Strong Certificate Mapping

Microsoft knowledge base article KB5014754, released in May of 2022, introduced changes to domain controllers to require strong certificate mapping when using certificates to authenticate to Active Directory (AD). It was initially deployed in compatibility mode, only warning administrators when certificates are used for authentication that aren’t strongly mapped. However, full enforcement is mandatory beginning with the September 2025 security updates. This requirement introduces some challenges when issuing certificates to the device using PKCS during Autopilot provisioning.

Intune PKCS Certificates

When using PKCS certificates and the Intune Certificate Connector, the endpoint’s on-premises AD security identifier (SID) is not added to the issued certificate during Autopilot. Interestingly, this does not happen when using SCEP certificates. If the device certificate is not strongly mapped, the Always On VPN device tunnel will still authenticate successfully because Always On VPN does not use AD to authenticate device connections. Instead, Always On VPN simply verifies the certificate (e.g., that it is not expired or revoked) and allows authentication if the certificate passes the validation.

However, enterprise Wi-Fi access may fail without strongly mapped certificates if device authentication is required. Also, there may be other scenarios where a device authentication certificate without strong mapping may cause authentication to fail.

Workarounds

There are a few ways to work around this limitation. Consider the following options.

Native Entra ID Join

The simplest way to avoid the challenges of PKCS certificates and Hybrid Entra join is to avoid it altogether in favor of native Entra join. However, this may not be an option for everyone.

Use SCEP

For some reason, certificates issued with SCEP do not suffer from this limitation. In my testing, SCEP certificates are always strongly mapped. However, deploying SCEP certificates is much more complex than using PKCS. (Pro tip: Cloud PKI for Intune uses SCEP and requires no configuration! It’s definitely something to consider.)

Short-Lived Certificates

Another option is to deploy temporary, short-lived certificates (valid for only a few days) using PKCS to ensure the Always On VPN device tunnel works, and then deploy a permanent, long-term certificate post-deployment that includes the strong mapping. To do this, administrators can leverage dynamic group assignments in Intune. For example, the administrator can assign the short-lived certificate to an Autopilot Provisioning devices group and later assign a long-term certificate to the Hybrid Joined devices group.

Here’s an example of the dynamic group membership configuration.

Autopilot Provisioning Devices:

(device.devicePhysicalIDs -any (_ -contains “[ZTDId]”)) -and (device.deviceTrustType -ne “ServerAD”)

Hybrid Entra Join Devices:

(device.deviceTrustType -eq “ServerAD”)

In this configuration, the initial PKCS certificate is deployed without the strong mapping when the endpoint is enrolled to Autopilot but has not yet joined the domain. During this time, the endpoint will only be a member of the Autopilot Provisioning Devices group and will receive the short-lived, temporary certificate. Later, once the endpoint has successfully joined the domain, the device will move from the provisioning group to the Hybrid Entra Join Devices group. When this happens, a permanent, strongly mapped long-term certificate is enrolled on the device.

Manual Certificate Mapping

Certificates can be manually mapped via the altSecurityIdentities property of the computer object in AD. Obviously, this doesn’t scale well, so my good friend Steve Prentice published a PowerShell script to automate this process. You can find more details and the script here.

Summary

Windows Autopilot streamlines device provisioning with Intune, but Hybrid Entra Join introduces challenges when PKCS certificates lack strong mapping during initial deployment, potentially disrupting VPN and Wi-Fi authentication. Administrators can avoid this by switching to native Entra join or by using workarounds such as switching to SCEP, using short-lived certificates, or manually mapping certificates.

Additional Information

KB5014754 – Certificate-based authentication changes on Windows domain controllers

How To: Map a user to a certificate via all methods available in the altSecurityIdentities attribute

Hybrid Autopilot: Automating altSecurityIdentities

Configure Microsoft Entra hybrid join

Overview: Cloud PKI for Microsoft Intune

Certificate Connector for Microsoft Intune Agent Certificate Renewal Failure

The Certificate Connector for Microsoft Intune is a vital component that allows administrators to issue and manage enterprise PKI certificates to endpoints managed by Microsoft Intune. The connector is installed on a Windows server with access to the on-premises Certificate Authority (CA). It is registered with Intune and can be used by any PKCS or SCEP device configuration profiles defined by Intune administrators.

Agent Certificate

When you install the Certificate Connector for Intune, a certificate issued by the Microsoft Intune ImportPFX Connector CA is automatically enrolled into the local computer certificate store of the server where the connector is installed. This certificate authenticates the connector to Intune and is valid for one year from the date of issuance. This certificate is automatically renewed in most cases. However, some configurations prevent this from happening.

Failed To Renew

Administrators may find event log errors with event ID 2 from the CertificateConnectors source in the Microsoft-Intune-CertificateConnectors operational event log with the following information.

Pki Create Service:

Failed to renew agent certificate

System.Security.Cryptography.CryptographicException: Access is denied.

Root Cause

Agent certificate renewal fails when the Certificate Connector for Intune is running under a service account that is not a member of the local administrators security group. You will not encounter this error if the connector services are running in the SYSTEM context, however.

Resolution

There are a few different ways to resolve this issue. Here are some options to consider.

Grant Admin Rights

Adding the service account under which the connector service runs will allow the agent certificate to renew automatically. However, this may not be desirable from a security perspective. To address this, administrators may temporarily grant local administrative access to renew the agent certificate, then revoke this permission once the certificate has been successfully renewed. However, this is a manual process that doesn’t scale well and requires annual administrative intervention.

Reinstall

Uninstalling and reinstalling the Certificate Connector for Intune will force a new certificate enrollment during the registration process. You can delete the old certificate after completing the installation.

Switch to SYSTEM

Changing from a service account to SYSTEM will also resolve this issue. However, it is not recommended to make these changes directly on the services themselves. Instead, administrators should remove and reinstall the Certificate Connector for Intune, selecting the SYSTEM option rather than the service account method.

Note: Using the SYSTEM account for the Certificate Connector for Intune should be avoided when using PKCS. Details here.

Summary

The Certificate Connector for Intune agent certificate renewal fails when the service is configured to run as a service account without local administrative rights. The best way to resolve this is to add the service account to the local administrators group on the server where the connector is installed. However, this isn’t always ideal. Although running the connector in the SYSTEM context is acceptable when using SCEP, it should be avoided when using PKCS. Administrators will have to accept the risk of the service account having local administrative rights or accept that they’ll have to reinstall the connector annually.

Additional Information

Certificate Connector for Intune Service Account and PKCS

Strong Certificate Mapping for Intune PKCS and SCEP Certificates

Intune Strong Certificate Mapping Error

Intune PKCS and SCEP Certificate Validity Period

Certificate Connector for Intune Failure

Certificate Connector for Intune Configuration Failed

Troubleshooting Intune Failed PKCS Request

Intune PKCS and SCEP Certificate Validity Period

With the recent announcement of drastically reduced certificate lifetimes for public TLS certificates, there has been much discussion about certificate lifetimes for private certification authorities (CAs) like Microsoft Active Directory Certificate Services (AD CS). Most commonly, AD CS certificates are issued with a one-year validity period. However, as I’ve discussed in the past, there’s good reason to consider shorter lifetimes in many scenarios. Reducing certificate lifetimes is a growing trend to enhance security, but it poses challenges for private CAs like AD CS. This post explains how to manage shorter certificate lifetimes in Intune using PKCS and SCEP.

AD CS Template

With AD CS, the administrator defines the certificate lifetime by setting the validity period value when creating the certificate template in Active Directory (AD), as shown here.

All certificates issued using this template will be valid for one year from the date of issuance.

Note: The only exception would be if the issuing CA’s certificate were due to expire before the one-year expiration date. In that case, the certificate would be valid until the CA certificate expires.

Intune PKCS and SCEP

When issuing certificates with Intune using either PKCS or SCEP, administrators deploy an Intune enrollment certificate template in AD that Intune uses for user and device certificate enrollment. While the Intune enrollment certificate template defines the default validity period, Intune also allows administrators to specify a desired validity period in the PKCS or SCEP policy settings, as shown here.

Intune Validity Period and AD CS

Although Intune provides the ability to define the validity period on the PKCS or SCEP policy, AD CS does not honor this setting unless explicitly configured to do so. Instead, it defaults to the period defined in the certificate template. Using the example above, the administrator defined a validity period of 1 month. However, since the Intune enrollment certificate template’s validity period was set to one year, a certificate valid for one year will be issued.

Override Template Settings

Fortunately, there is a way to override this default behavior. On the issuing CA where the Intune enrollment certificate template is published, open an elevated PowerShell command window and run the following command.

certutil.exe -setreg Policy\EditFlags +EDITF_ATTRIBUTEENDDATE

Once complete, run the following PowerShell command to restart the CA service.

Restart-Service -Name CertSvc -PassThru

After making this change, administrators can define a shorter certificate validity period than specified on the template using Intune PKCS and SCEP policies.

Note: For security reasons, this setting only allows requests that are shorter than the template’s defined validity period. You cannot request a certificate with a validity period that is longer than the template allows.

Summary

By enabling the EDITF_ATTRIBUTEENDDATE flag on your issuing CA, you gain flexibility to tailor certificate validity periods per use case—while still enforcing a maximum validity via the AD Intune certificate enrollment template. Flexible certificate validity periods are especially valuable in environments that are moving toward short-lived certificates for improved security posture.

Additional Information

TLS Certificate Lifetimes Will Officially Reduce to 47 Days

Always On VPN SSTP and 47-Day TLS Certificates

The Case for Short-Lived Certificates in Enterprise Environments

Mastering Certificates with Microsoft Intune – Live Online Training

The Case for Short-Lived Certificates in Enterprise Environments

Digital certificates, issued by an internal, private Certification Authority (CA) like Microsoft Active Directory Certificate Services (AD CS), are commonly used in enterprise environments for user and device authentication for workloads such as VPN, Wi-Fi (802.1x), System Center Configuration Manager (SCCM), IPsec, and more. But how long should a user or device authentication certificate be valid? This question is increasingly critical as organizations strive to balance security and operational efficiency. Short-lived certificates, typically valid for weeks or months rather than years, are gaining traction as a powerful tool to enhance security. By reducing the window of opportunity for attackers to exploit compromised credentials, short-lived certificates offer a proactive approach to mitigating risks while aligning with evolving security best practices and the needs of modern IT infrastructures.

What is a Certificate?

A digital certificate is a document that binds an identity to an asymmetric key pair (public key and private key). Certificates offer strong, phishing-resistant authentication that improves security and assurance for users and devices authenticating to Microsoft Active Directory (AD). When a certificate is issued, an administrator decides how long the certificate will be valid. The criticality of this setting is often overlooked.

Certificate Lifetime

Administrators must define the certificate’s validity period when creating a certificate template in AD CS or an Intune PKCS or SCEP device configuration policy. Most commonly, administrators select the default one-year validity period. However, public CAs are trending toward shorter certificate lifetimes, and strong consideration should be given to their use in private enterprise deployments.

Current Standards

Today, the maximum certificate lifetime for a publicly issued TLS certificate is 398 days (approximately 13 months). This standard is imposed by the CA/Browser Forum, a voluntary consortium of public CAs, browser vendors, and other industry stakeholders that develop and promote security standards and best practices for digital certificates and Public Key Infrastructure (PKI). They established the 398-day certificate lifetime mainly in response to the previous decade’s plethora of SSL/TLS vulnerabilities.

Challenges

Having certificates with long lifetimes poses significant challenges for administrators when responding to key compromise events or zero-day vulnerabilities. This may necessitate urgent certificate replacement, often involving manual intervention. To address these challenges and promote automation, some public CAs like Let’s Encrypt issue certificates with much shorter lifetimes than one year.

Public CA Certificates

Shorter lifetimes for public SSL/TLS certificates have numerous positive security benefits. Short-lived certificates provide agility to update cryptography settings more rapidly than long-lived certificates. Also, the short lifetime of the certificate is beneficial if the private key is compromised because it limits the amount of time an attacker can exploit the stolen key, limiting exposure and reducing potential damage. These security benefits have driven significant changes in public CA practices, as seen in today’s standards.

47 Days

Recently, I wrote about a new directive from the CA/Browser Forum, which adopted a measure reducing the current maximum lifetime of public TLS certificates to 47 days. The maximum lifetime for public TLS certificates will be gradually reduced to allow the industry to adopt short-lived certificates.

Enterprise CA Certificates

Private enterprise PKI deployments like AD CS are not required to adhere to CA/Browser Forum mandates. Organizations are free to manage their internal PKI however they choose. However, examining industry trends and ensuring that security best practices are aligned as much as possible is crucial. While public CAs set the pace, private enterprise PKI can adopt similar strategies to bolster security.

AD Authentication

As stated previously, many positive security benefits are associated with short-lived certificates, especially for authentication to Active Directory.

PKINIT

PKINIT is an extension to the Kerberos protocol that enables certificate-based authentication with Active Directory (AD). You can read about the details here, but PKINIT allows a principal (user or device) to authenticate to AD by simply demonstrating control of the private key. Thus, protecting the private key is vital.

TPM

Enrolling certificates in a Trusted Platform Module (TPM) is the best way to ensure private keys remain private. No one, including administrators, can export private keys protected by TPM. Administrators should ensure TPM enrollment for client authentication certificates whenever possible.

Guidance

Today, I recommend that my customers issue end entity user and device authentication certificates with a lifetime of no more than one year for 2048-bit RSA certificates with private keys stored on TPM. However, there are important considerations and compelling advantages to using much shorter lifetime certificates.

Best Practice

General use client authentication certificates should be enrolled to TPM without exception and have a valid lifetime of no more than one year. However, there is still value in using shorter lifetime certificates, even with TPM. For example, short-lived certificates ensure timely renewal, which can be helpful when implementing changes to certificate templates. A perfect example of this is the changes required to support KB5014754. Administrators may wish to use certificates with validity periods of less than one year to ensure timely replication of certificate settings changes and to provide more frequent key rotation.

Non-TPM

There may be scenarios where a client authentication certificate must be issued to a device without a TPM. Examples include virtual machines without TPM, VDI deployments, and legacy devices. These cases should be treated as exceptions and managed accordingly. Consider shortening the lifetime of non-TPM certificates to 90 days or less.

Privileged Users

Administrators or other privileged accounts enrolling for certificates can benefit from even shorter validity periods. Consider issuing client authentication certificates to these users with certificate lifetimes of 30 days or less.

Considerations

Short-lived certificates aren’t always ideal in all cases. For example, consider a scenario where a user or device is offline for a prolonged period, such as extended vacations, maternity or paternity leave, or sabbaticals. Users may experience issues accessing resources after returning from an extended absence. Of course, if they can re-enroll for certificates, this shouldn’t be a problem. For AD CS, it means connectivity to an enterprise issuing CA server. Intune-managed endpoints simply need Internet access to obtain a new certificate.

Automation

Working with short-lived certificates manually is infeasible. Automation is the key to success with short-lived certificates. For client authentication certificates issued on-premises, enabling certificate autoenrollment via group policy ensures that all domain-joined devices enroll and renew their certificates automatically. Certificates deployed and managed using Microsoft Intune are automated by default.

Summary

The next time you create a certificate template in AD CS or Intune, consider the certificate lifetime. Recommended best practice is no more than one year validity period for 2048-bit RSA end-entity certificates with hardware-backed key storage. However, consider shorter validity periods for those cases where it makes sense. Prioritize TPM enrollment and put additional controls in place for exceptions. Ensure automated enrollment and renewal are in place to reduce administrative overhead. Following the guidance outlined above, your organization will reduce its attack surface and limit exposure to compromised certificates.

More Information

If you’d like to learn more about implementing short-lived certificates in your organization, fill out the form below, and I’ll provide more information.

References

Digital Certificates for Strong Authentication

Digital Certificates and TPM

Drawbacks of Multifactor Authentication

Public Key Cryptography for Initial Authentication (PKINIT) in Kerberos Protocol

Always On VPN Authentication Failure After February 2025 Security Update

Microsoft introduced changes to Windows domain controllers in the February 2025 security update that may result in authentication failures for Always On VPN user tunnel connections. If you suddenly find that all your Always On VPN user tunnel connections fail, additional changes may be required to resolve the issue.

Authentication Failure

Administrators may find that Always On VPN connections fail after applying the February 2025 Microsoft security updates. Specifically, users may receive the following warning message.

“The remote access connection completed, but authentication failed because the certificate that authenticates the client to the server is not valid. Ensure that the certificate used for authentication is valid.”

Error 853

Administrators will also find a corresponding event log entry with event ID 20227 from the RasClient source with the following error message.

“The user <username> dialed a connection named <connection name> which has failed. The error code returned on failure is 853.”

NPS Events

The event log on the NPS server will also record event ID 6273 from the Microsoft Windows security auditing source with the following error message.

“Network Policy Server denied access to a user.”

The authentication details of the event include Reason Code 16 with the following reason.

“Authentication failed due to a user credentials mismatch. Either the user name provided does not map to an existing user account or the password was incorrect.”

DC Events

If the issue is related to changes implemented to domain controllers in the February 2025 security update, administrators will also find a corresponding event log entry on a domain controller with event ID 39 from the Kerberos-Key-Distribution-Center source with the following error message.

“The Key Distribution Center (KDC) encountered a user certificate that was valid but could not be mapped to a user in a secure way (such as via explicit mapping, key trust mapping, or a SID). Such certificates should either be replaced or mapped directly to the user via explicit mapping.”

Root Cause

The above conditions indicate that a user attempted to authenticate to the VPN with a certificate that was not strongly mapped. Most likely, the certificate was issued using Microsoft Intune with SCEP or PKCS. This results from changes made to domain controllers in the February 2025 security update that requires certificates used for Active Directory authentication to be strongly mapped. Until now, domain controllers allowed access and only logged an event in the event log when a certificate did not include strong certificate mapping. The February 2025 security update now enforces strong certificate mapping, and authentication requests will fail without it.

Resolution

Administrators must issue new certificates that are strongly mapped to resolve this issue. For certificates issued with PKCS, changes are required on the Intune Certificate Connector server before re-issuing. For certificates issued with SCEP, changes to the device configuration policy are required. See the post Strong Certificate Mapping for Intune PKCS and SCEP Certificates for more details.

Workaround

Re-issuing certificates takes time. To restore connectivity immediately, administrators can implement the following registry settings on all domain controllers to switch back to audit mode and allow authentication without strong certificate mapping.

Key: HKLM:\SYSTEM\CurrentControlSet\Services\Kdc
Name: StrongCertificateBindingEnforcement
Type: DWORD
Value: 1

I recommend deploying this setting via GPO assigned to the Domain Controllers OU. However, you can also implement this change using PowerShell if necessary.

New-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Services\Kdc’ -Name ‘StrongCertificateBindingEnforcement’ -PropertyType DWORD -Value 1 -Force

Additional Information

Strong Certificate Mapping for Intune PKCS and SCEP Certificates

Strong Certificate Mapping Enforcement February 2025

Certificate-Based Authentication Changes and Always On VPN

Intune Strong Certificate Mapping Error

Strong Certificate Mapping Error with PKCS

Arizona Systems Management User Group March 2025

I’m excited to announce that I’ll be speaking at the Arizona Systems Management User Group (AZSMUG) at their next user group meeting on Friday, March 7, at 9:00 AM MST. I am presenting on the topic of Certificate Deployment Strategies with Microsoft Intune.

Intune and Certificates

My session at AZSMUG will provide an overview of issuing and managing certificates with Microsoft Intune. We’ll begin by examining common scenarios for certificate authentication and explore various delivery methods, including PKCS and SCEP. Additionally, we’ll discuss supporting technologies such as the Network Device Enrollment Service (NDES) and review deployment strategies and high availability options for the Intune Certificate Connector. The session will also cover Cloud PKI for Intune, integration with on-premises Active Directory, and best practices for securing certificate lifecycles and key management in enterprise environments.

Register Now

If you are in the Phoenix area and would like to attend the user group meeting on Friday, March 7, you will find the registration link here. Hope to see you there!

Additional Information

Arizona Systems Management User Group

Intune and Certificates Masterclass

Always On VPN Intermittent 13801 Error

Always On VPN error 13801 is common when establishing an IKEv2 VPN connection. Typically, the issue is related to a configuration error or a problem with certificate deployment. However, administrators may encounter the 13801, an IKE authentication error, intermittently. Configuration errors are binary. If there is a misconfiguration, IKEv2 never works at all. However, a configuration error seems unlikely since the connection works occasionally yet fails at other times.

Client Authentication

The minimum application policy (Enhanced Key Usage, or EKU) requirement for the device authentication certificate for IKEv2 is Client Authentication (1.3.6.1.5.5.7.3.2). When intermittent 13801 errors occur, administrators may find multiple certificates in the local computer certificate store with the Client Authentication EKU issued by different certificate authorities. Commonly, Intune-managed Windows devices may include several certificates with Client Authentication.

Certificate Selection

When Windows attempts to establish an Always On VPN IKEv2 connection, and there are multiple certificates in the local computer certificate with Client Authentication defined, Windows must choose one certificate to use for the connection. If Windows chooses incorrectly, you will receive the 13801 IKE authentication failure error. If Windows selects the right one, the connection succeeds.

Resolution

There are several ways to resolve this issue. The best way is to update the Always On VPN device authentication certificate to include the IP security IKE intermediate application policy (EKU). When Windows encounters multiple client authentication certificates in the local computer certificate store, it will prefer any certificate with the IP security IKE intermediate application policy for IKEv2 VPN connections. Including the IP security IKE intermediate application policy on the Always On VPN device authentication certificate ensures proper certificate selection when multiple client authentication certificates are present.

Note: This change must be made to the Intune certificate enrollment template when using Intune with PKCS or SCEP.

Certificate Template

To update an existing Always On VPN device authentication certificate to include the IP security IKE intermediate application policy, open the certificate templates management console (certtmpl.msc) and perform the following steps.

  1. Right-click the VPN device authentication certificate template and choose Properties.
  2. Select the Extensions tab.
  3. Click on Application Policies.
  4. Click Edit.
  5. Click Add.
  6. Select the IP security IKE intermediate application policy.
  7. Click Ok.
  8. Click Ok.
  9. Click Ok.

Once complete, any certificates issued after this change is applied will now include the IP security Ike intermediate application policy.

Force Renewal

Administrators may wish to update all certificates immediately rather than wait until they renew to receive the new setting. The course of action depends on how certificates are issued.

On-Premises

When issuing certificates using Active Directory Certificate Services (AD CS) on-premises, right-click the Always On VPN device authentication certificate template and choose Reenroll All Certificate Holders. This will force all domain-joined clients with Autoenroll permissions on the template to renew their certificate on their next enrollment cycle, regardless of the certificate’s lifetime.

Intune

Follow the steps below to force re-enrollment for all certificate holders when deploying certificates using Intune.

SCEP – Add the IP Security IKE Intermediate application policy to the Intune VPN policy. After this change is applied, Intune will reenroll all endpoints.

PKCS – A new Intune device configuration policy must be created that includes the IP security IKE intermediate application policy. Assign the new policy and remove the old one to replace all certificates.

PowerShell

It’s also possible to resolve this issue using PowerShell. Administrators can use the Set-VpnConnection PowerShell cmdlet to select a certificate based on the root certification authority (CA) or a specific custom application policy defined on the Always On VPN device authentication certificate. Be sure to add the -AllUserConnection switch when working with the device tunnel.

Root CA

Open a PowerShell command window and run the following command.

$RootCA = Get-Child-Item -Path Cert:\LocalMachine\My\<thumbprint of root CA certificate>
Set-VpnConnection -Name <name of VPN profile> -MachineCertificateIssuerFilter $RootCA

Application Policy

Open a PowerShell command window and run the following command.

Set-VpnConnection -Name <name of VPN profile> -MachineCertificateEKUFilter <OID>

Note: When using a custom application policy Windows will return a warning message stating the EKU could not be validated. You can safely disregard this warning.

Intune Remediation

While running PowerShell commands locally might be helpful for troubleshooting and targeted evaluation testing, deploying settings via PowerShell at scale is challenging. For those organizations managing their devices using Microsoft Intune, I’ve published a few detection and remediation scripts on GitHub to perform these tasks.

Summary

The intermittent Always On VPN 13801 IKE authentication credentials are unacceptable error message is best resolved by updating the Always On VPN device authentication certificate to include the IP security IKE intermediate application policy (EKU). Although using PowerShell also works, it doesn’t scale effectively. SCCM or Intune remediations can help, but I’d encourage you to update the certificate template as best practice instead.

Additional Information

Troubleshooting Always On VPN Error 13801

Troubleshooting Always On VPN Error 13806

Troubleshooting Always On VPN Error 13868