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

Microsoft Intune Certificate Connector Configuration Failed – String Cannot Be of Zero Length

When deploying on-premises enterprise PKI certificates using Microsoft Intune with Simple Certificate Enrollment Protocol (SCEP) certificate profiles, administrators must deploy a Windows Server with the Network Device Enrollment Service (NDES) role installed. Once configured, the Microsoft Intune Certificate Connector can be installed and configured to allow administrators to issue and manage certificates for their Intune-managed endpoints.

Configuration Failed

After configuring NDES, administrators may encounter an error message when installing the Microsoft Intune Certificate Connector. The message states:

Configuration Failed

Configuring Microsoft Intune Certificate Connector failed. No changes were made to Feature or Proxy settings. Please try again.

Unexpected Failure. Error: System.ArgumentException: String cannot be of zero length.
Parameter name: name
at System.Security. PrincipaI.NTAccount..ctor(String name)
at Microsoft.lntune.Connectors.ConfigUlScep.SetServiceUserPermissions(String username)
at Microsoft.lntune.Connectors.ConfigUlScep.SetNdesUserPermissions(String username)
at Microsoft.lntune.Connectors.ConfigUlScep.Enable()
at Microsoft.Intune.Connectors.ConfigUI.ApplyConfiguration.<ApplyChanges>d__10.MoveNext()

Missing Service Account

This error occurs because the administrator configured the NDES role using the default application pool identity, which the Intune Certificate connector does not support.

Resolution

To resolve this issue, configure the SCEP application pool to run as a Group Managed Service Account (gMSA), which is a security best practice. Alternatively, you can configure the SCEP application pool to run as a regular domain service account (not recommended).

SCEP Application Pool Configuration

To update the SCEP application pool to run as a gMSA or domain service account, add the service account to the IIS_IUSRS group. If running as a domain service account and not a gMSA, be sure to also grant the service account the Logon as a Service right.

Next, open Internet Information Services (IIS) Manager (inetmgr.exe) and follow the steps below.

  1. Expand the NDES server in the navigation tree.
  2. Highlight Application Pools.
  3. Right-click the SCEP application pool and choose Advanced Settings.
  4. In the Process Model section, highlight Identity.
  5. Click the ellipses next to ApplicationPoolIdentity.
  6. Select Custom account.
  7. Click Set.
  8. Enter the service account using the domain\username format. Be sure to include the trailing $ when specifying a gMSA.
  9. If using a standard domain service account, enter and confirm the password.
  10. Click Ok three times.
  11. Finally, stop and start the application pool for the changes to take effect.

Note: Using a gMSA requires additional configuration in the domain. Details here.

Once complete, be sure to assign the Request Certificates permission to the gMSA or domain service account on the issuing certification authority (CA) server. In addition, assign Enroll permission to the service account on the NDES certificate template in Active Directory (AD).

Intune Certificate Connector

The Intune Certificate Connector does not support running under a gMSA. However, when using NDES/SCEP, it’s acceptable to run the connector service under the SYSTEM account. Ensure the connector server’s computer account is granted Issue and Manage Certificates permissions on the issuing CA server.

Summary

For NDES used with Intune SCEP certificate profiles, a group Managed Service Account (gMSA) is the preferred service account. A standard domain user account is supported if a gMSA is not an option. Specify the account when you configure the NDES role or leave the default ApplicationPoolIdentity and replace it with the gMSA before installing the Intune Certificate Connector.

Additional Information

Microsoft NDES Information Disclosure: Detection and Remediation

Microsoft NDES Security Hardening: Protecting and Monitoring the SCEP Registry Configuration

Troubleshooting NDES Error 0x80070003 Path Not Found on Windows Server 2025

Troubleshooting NDES Error 0x80094800 Unsupported Cert Type on Windows Server 2025

Training: Mastering Enterprise PKI Certificates with Microsoft Intune

NDES Security Hardening: Protecting and Monitoring the SCEP Registry Configuration

The Active Directory Certificate Services (AD CS) Network Device Enrollment Service (NDES) is widely deployed to support the issuance and management of enterprise PKI certificates via Microsoft Intune and the Intune Certificate Connector. NDES relies on registry settings to identify its issuing CA, certificate templates, and other SCEP configuration parameters. An attacker with sufficient access to an NDES server could alter these settings and redirect enrollment to another template published on the issuing CA and accessible to the NDES service account. Because enrollment might continue without an obvious service failure, administrators could overlook the change. This article explains how to restrict access to the MSCEP registry key, audit modifications, and use Sysmon to collect additional investigative context.

Understanding the MSCEP Registry Configuration

NDES stores its core SCEP configuration under the HKLM\SOFTWARE\Microsoft\Cryptography\MSCEP registry key. These settings identify the issuing CA and certificate templates used for enrollment and control other aspects of NDES operation. Because they directly influence how certificate requests are processed, unauthorized changes could alter enrollment behavior without modifying the NDES application itself.

Enrollment Templates

NDES uses the following registry values to identify the certificate templates used for SCEP enrollment.

HKLM\SOFTWARE\Microsoft\Cryptography\MSCEP\EncryptionTemplate
HKLM\SOFTWARE\Microsoft\Cryptography\MSCEP\GeneralPurposeTemplate
HKLM\SOFTWARE\Microsoft\Cryptography\MSCEP\SignatureTemplate

In many deployments, all three values reference the same template. If the environment supports distinct signature, encryption, or general-purpose enrollment scenarios, each value can reference a template designed for that specific purpose.

Additional MSCEP Settings

The MSCEP key contains more than certificate template assignments. Its CAInfo and CAType subkeys identify the CA to which NDES submits requests, while other subkeys control settings such as the hash algorithm and capabilities advertised to SCEP clients.

Information Disclosure and Reconnaissance

The default permissions for the MSCEP registry key are inherited from HKLM\SOFTWARE, which grants the local Users group read access. This allows locally authenticated users, as well as users granted remote registry access, to read the template names and CA configuration. Template names can aid reconnaissance, as an attacker can query Active Directory for the corresponding template definitions and evaluate their configurations against known AD CS escalation techniques. The CAInfo subkey can also disclose the internal fully qualified domain name of the issuing CA. Restricting access to the MSCEP key reduces unnecessary exposure of this information.

Why the MSCEP Key Is an Effective Monitoring Target

After NDES is deployed to production, these values should change only during planned reconfiguration. This makes the MSCEP key a high-value, low-noise monitoring target. Legitimate modifications should be rare and documented, while any unexpected change warrants immediate investigation.

Before You Begin

The changes described in this article modify access permissions and configure auditing for registry settings that NDES requires. An incorrect service identity, incomplete allowlist, or unsupported environmental assumption can prevent certificate enrollment. Test these changes in a nonproduction environment first, confirm that you have a working backup and rollback procedure, and validate successful enrollment before applying them broadly. Adapt the examples to your environment and follow your organization’s change management and security review processes.

In addition, be sure to back up the configuration before making any changes. A full server backup or a virtual machine snapshot is helpful. However, administrators can perform additional steps to save information before altering the default settings.

Determine the NDES Service Account

The permissions applied below grant access to the account used by the SCEP application pool. Confirm this account before proceeding by opening IIS Manager (inetmgr.exe), expanding the IIS server, and selecting Application Pools. Highlight the SCEP application pool and note the account shown in the Identity column.

Back Up the Current Permissions

A registry export with reg.exe captures data but not the security descriptor, so it is not a rollback for this change. Run the following PowerShell commands to capture the descriptor in SDDL format instead.

$Key = 'HKLM:\SOFTWARE\Microsoft\Cryptography\MSCEP'
(Get-Acl -Path $Key -Audit).Sddl | Out-File -FilePath .\mscep-acl-backup.txt -Encoding utf8

The rollback process is covered later in this post.

Restricting Access to the MSCEP Key

For a dedicated NDES server, restrict the MSCEP key to SYSTEM, the local Administrators group, and the identity used by the SCEP application pool. All other access entries should be removed, including the inherited Read permission for the local Users group. If another service identity requires access in your environment, such as a domain service account used by the Intune Certificate Connector, account for it in both the explicit access rules and the allowlist before applying the changes.

Administrators must retain full control. Even if the Administrators entry were removed, a local administrator could exercise the necessary privileges to take ownership of the key and rewrite its permissions. The ACL therefore reduces unnecessary access but does not provide a security boundary against a local administrator or an attacker with equivalent privileges. This is why the auditing described in the next section is an important complementary control.

Important Note: Registry values do not carry their own security descriptors, so the permissions applied here govern the MSCEP key, every value in it, and every subkey beneath it. The service identity is granted full control rather than read because NDES writes to this key during normal operation, and read-only access will break it.

Removing Inheritance

The inherited entries from HKLM\SOFTWARE are where the broad access comes from, so they must be removed first. On the NDES server, open an elevated PowerShell command window and run the following commands.

$Acl = Get-Acl -Path $Key -Audit
$Acl.SetAccessRuleProtection($True, $False)

The -Audit parameter reads the system access control list (SACL) and the discretionary access control list (DACL), so both can be updated and committed in a single write later. The second parameter of SetAccessRuleProtection is set to false, which discards the inherited entries rather than converting them to explicit copies. This approach is intentional. Inherited entries cannot be removed with PurgeAccessRules method, so preserving them would leave the broad grants in place and defeat the entire exercise. No explicit deny entry is required anywhere in this process. After this change, the local Users group has no access to the key at all.

Granting Explicit Access

Breaking inheritance also removes the SYSTEM and Administrators grants, so our explicit entries will replace them. Well-known security identifiers (SIDs) are used instead of account names, so this works correctly on non-English Windows installations.

$ServiceIdentity = 'corp\gmsa_ndes$'   # or 'corp\svc_ndes' if using a domain service account
$Sid = (New-Object System.Security.Principal.NTAccount($ServiceIdentity)).Translate([System.Security.Principal.SecurityIdentifier])
ForEach ($Identity in @('S-1-5-18', 'S-1-5-32-544', $Sid.Value)) {
    $Trustee = New-Object System.Security.Principal.SecurityIdentifier($Identity)
    $Acl.AddAccessRule((New-Object System.Security.AccessControl.RegistryAccessRule($Trustee, 'FullControl', 'ContainerInherit', 'None', 'Allow')))
}

S-1-5-18 is the well-known SID for SYSTEM, and S-1-5-32-544 is the well-known SID for the local Administrators group. ContainerInherit ensures the rights propagate to the subkeys.

Removing Unapproved Access Entries

The remaining explicit entries are evaluated against an allowlist, and anything that does not belong to those three identities is purged.

$AllowedSids = @('S-1-5-18', 'S-1-5-32-544', $Sid.Value)
ForEach ($Entry in ($Acl.Access | Where-Object { -not $_.IsInherited } | Select-Object -ExpandProperty IdentityReference -Unique)) {
    If ($Entry -is [System.Security.Principal.SecurityIdentifier]) {
        $EntrySid = $Entry
}
Else {
        $EntrySid = $Entry.Translate([System.Security.Principal.SecurityIdentifier])   
}
   
If ($AllowedSids -notcontains $EntrySid.Value) {
        $Acl.PurgeAccessRules($EntrySid)   
}
}

Sweeping against an allowlist rather than purging a fixed list of known principals removes application capability SIDs, CREATOR OWNER, any application pool entry that no longer matches the current SCEP application pool service account, and anything left over from previous administrative changes, without enumerating them in advance. It also makes the operation repeatable, so running it a second time on an already hardened server produces the same result.

Important Note: This code uses SID comparison. Identity references can be returned as either an NTAccount or a SecurityIdentifier, depending on whether the account resolves, so comparing by name will silently miss orphaned entries.

Auditing Changes to the MSCEP Key

Restricting the ACL reduces unnecessary access, but it cannot prevent a local administrator from taking ownership or rewriting the permissions. Auditing provides a complementary detective control by recording attempts to modify the key.

Add the Registry Audit Rule

To enable auditing, add an audit rule to the MSCEP key’s SACL that records successful and failed attempts by any identity to modify its values, subkeys, or permissions. Then commit the DACL and SACL together.

$Everyone = New-Object System.Security.Principal.SecurityIdentifier('S-1-1-0')
$AuditRule = New-Object System.Security.AccessControl.RegistryAuditRule($Everyone, 'SetValue, CreateSubKey, Delete, ChangePermissions, TakeOwnership', 'ContainerInherit', 'None', 'Success, Failure')
$Acl.AddAuditRule($AuditRule)
Set-Acl -Path $Key -AclObject $Acl

The audited operations are limited to changes. Specifically, setting a value, creating or deleting a subkey, changing permissions, and taking ownership. Reads are intentionally not audited. The three identities that still have access read these values routinely, so auditing that activity would generate excessive noise. Note that failure auditing applies only to the listed modification rights, so a denied read attempt will not be logged.

In addition, TakeOwnership and ChangePermissions are included deliberately because an attempt to alter the key’s security descriptor could indicate that someone is trying to weaken or bypass the applied controls. These operations should be rare after deployment and warrant investigation when they are not associated with an approved administrative change.

Recycle the SCEP Application Pool

Once the permissions are committed, recycle the SCEP application pool to close any existing registry handles and ensure the worker process reopens the MSCEP key under the new access controls.

Restart-WebAppPool -Name SCEP

Enable the Registry Audit Subcategory

An audit rule on its own does not generate events. The Object Access category must have the Registry subcategory enabled before Windows will write anything to the Security event log. Confirm the current setting by running the following command.

auditpol.exe /get /subcategory:"{0CCE921E-69AE-11D9-BED3-505054503030}" /r

The subcategory is referenced by GUID rather than by name for locale independence. If it is not enabled, enable it through Group Policy under Advanced Audit Policy Configuration > Object Access > Audit Registry rather than setting it locally, so the setting survives and applies consistently across your NDES infrastructure.

Recommended Security Alerts

With the Registry audit subcategory and the SACL configured as described, creating, deleting, or modifying a registry value under the MSCEP key generates event ID 4657 in the Security event log, identifying the account, the value name, and both the old and new data. That last detail is what makes the event immediately actionable. You do not have to look up what the template was supposed to be, because the event tells you what it was and what it was changed to.

My recommendation is to alert on every event ID 4657 associated with EncryptionTemplate, GeneralPurposeTemplate, or SignatureTemplate values rather than attempting to tune out individual processes or accounts. These values should remain static after deployment, so their expected change volume is zero. Monitor modifications elsewhere under the MSCEP path as well but establish a baseline before treating every such event as an alert because some NDES configurations may update other values or subkeys during normal operation.

Additional Alerts

Two additional events are worth correlating when one of these fires:

  • Event ID 4670 records a change to the permissions on the object. On a hardened key, this is a strong signal, since it means someone modified the ACL you just applied.
  • An application pool recycle or an IIS restart shortly after a value change is the corroborating signal. Because NDES caches the template configuration in the worker process, a substituted template does not take effect until the SCEP application pool or server restarts. An attacker seeking immediate activation would therefore need to trigger a recycle or restart, creating another potentially observable event. Otherwise, the change could take effect later during a routine recycle or restart.

Add Process Context with Sysmon

Security event ID 4657 identifies the account, process name, process ID, registry value, and old and new data associated with a change. However, it does not provide the full command line, process lineage, hashes, or surrounding activity needed for a more complete investigation. The System Monitor (sysmon.exe) utility from the Microsoft Sysinternals suite supplements the Security event log with this information.

Sysmon is not a replacement for SACL. The Security event records the authorization decision as Windows made it, which is the authoritative record. Sysmon records the process lineage around that decision. The two sources are complementary. Sysmon can capture the process that triggers an application pool recycle or an IIS restart when that activity matches the configured process creation rules.

Sample Sysmon Configuration for NDES

I have published a sample Sysmon configuration for NDES servers on GitHub. It is available here. This targeted configuration monitors SCEP enrollment settings, IIS application pool activity, registration authority certificates and private keys, credential access, and selected AD CS, certificate store, IIS, and operating-system security events relevant to an NDES deployment. It is not intended to serve as a general enterprise baseline. You can run it as a standalone configuration on an NDES server or merge its rule groups into an existing baseline such as SwiftOnSecurity or Olaf Hartong sysmon-modular.

Install or Update Sysmon

After reviewing and testing the sample configuration, install Sysmon or apply the configuration to an existing Sysmon deployment. To install Sysmon, open an elevated command window and run the following command.

sysmon.exe -accepteula -i sysmon-ndes.xml

To update an existing installation and confirm the active configuration, run the following commands.

sysmon.exe -c sysmon-ndes.xml
sysmon.exe -c

Sysmon events are written to the following event log location.

Applications and Services Logs > Microsoft > Windows > Sysmon > Operational.

Sysmon Monitoring Coverage

The configuration is centered on detecting changes to security-sensitive registry locations. The remaining rules capture the process, file, network, and system activity needed to investigate those changes.

  • Registry events 12, 13, and 14 cover the MSCEP key and its subkeys using a contains condition so both the native and WOW6432Node paths are captured. The same rule group covers the Certificate Services configuration key, machine certificate stores and trust anchors, SCHANNEL and TLS configuration, IIS service configuration, and common persistence locations.
  • Process creation events capture the tools used to make these changes, including reg.exe, regedit.exe, certutil.exe, appcmd.exe, and iisreset.exe. Tools such as appcmd.exe and iisreset.exe, as well as PowerShell commands such as Restart-WebAppPool, can recycle the SCEP application pool or restart IIS, allowing a modified template configuration to take effect. Sysmon can capture these actions when the initiating process and command line match the configured process-creation rules. PowerShell Script Block Logging provides additional visibility into commands executed within an existing PowerShell session, which might not be captured as separate Sysmon process-creation events.
  • Process access events are restricted to handle requests against LSASS with the access masks commonly associated with credential dumping. On a host that holds registration authority private keys and runs under a gMSA identity, this is the single highest-value rule.
  • File creation and deletion events cover the private key containers under Crypto\RSA, Crypto\Keys, and Crypto\PCPKSP, the IIS configuration directory, and certificate file extensions. Web content extensions such as .aspx and .ashx are also included, because a file with one of those extensions appearing under the NDES site is a strong indicator of a web shell.
  • Network connection events are purposefully scoped to scripting hosts and file transfer utilities rather than everything. An NDES server constantly talks to the CA and enrolling clients, and logging all of it produces excessive noise and provides little insight.
  • Named pipe, WMI, and process tampering events are also included. Legitimate volume for these is close to zero on a dedicated NDES server, so they are logged in full.

Note: The registry rule group includes an exclusion for the highest-volume legitimate writers, such as services.exe, svchost.exe, and TrustedInstaller.exe, as well as CreateKey events. Without those exclusions, useful events are buried within minutes. However, broad process-based exclusions can create visibility gaps. Administrators should validate that those exclusions do not suppress meaningful changes to the monitored paths.

Correlating Sysmon and Security Log Events

When a template value is modified, the Security event log records event ID 4657 with the account, value name, and old and new data. Sysmon records event ID 13 for the same operation, including the image path and process GUID associated with the write. If Sysmon also captured the corresponding process-creation event, the process GUID can be used to correlate event ID 13 with event ID 1, which provides the full command line and parent-process information. The Security event identifies the audited account and registry change, while Sysmon supplies richer process lineage and surrounding activity.

Sysmon Deployment Considerations

Before deploying this configuration, confirm that it is compatible with your installed Sysmon version and existing monitoring baseline. Test it on a representative NDES server first, then review the resulting event volume and adjust only those rules that conflict with known, legitimate activity.

  • Confirm the schema version supported by your installed Sysmon build by running
    sysmon.exe -s before deployment. The sample configuration uses schema version 4.90 and therefore requires Sysmon 15 or later.
  • The FileBlockExecutable rules actively block matching executable files rather than merely recording their creation. Review and test these rules carefully before deploying the configuration in production.
  • If you already run a Sysmon baseline, merge these rule groups into it rather than installing this configuration over the top of it. Installing a new configuration replaces the existing one entirely.
  • Forward both the Sysmon Operational event log and the Security event log to your Security Information and Event Management (SIEM) platform. Local event logs on a compromised server hosting an Internet-published SCEP endpoint are of limited investigative value, and an alert that nobody receives provides little protection.
  • Validate the configuration in a lab first. Sysmon rule evaluation order is not always intuitive, and an overly broad include rule on a busy server can generate a surprising amount of data.

NDES Operational Considerations

Tightening permissions on a key that a running service depends on has consequences worth understanding before you make these changes in production.

  • If the Intune Certificate Connector service runs as a custom account rather than SYSTEM, add that account to the allowlist and grant it read access. Check the logon account on the connector service before you begin. In this scenario, I recommend running the Intune Certificate Connector as SYSTEM to follow security best practices.
  • If you change the SCEP application pool identity later, NDES will fail until the key permissions are updated to include the new identity. These permissions are aligned to a specific account, so any change to that account requires a corresponding change here.
  • If you operate multiple NDES servers, apply these changes to all of them to ensure full coverage.
  • Document any planned change to the template configuration in your change management process. If you alert on these events as recommended, someone will need to close the ticket the alert generates.

Validate Permissions, Auditing, and Enrollment

Run the following PowerShell command to verify the resulting access rules.

(Get-Acl -Path $Key).Access | Format-Table IdentityReference, RegistryRights, IsInherited

Only SYSTEM, BUILTIN\Administrators, and the NDES service account identity should be listed, and none of the entries should be inherited. Next, run the following command to confirm the audit rule is present.

(Get-Acl -Path $Key -Audit).Audit

With the Registry audit subcategory enabled, perform a controlled test in a lab by changing a template value and recycling the SCEP application pool. Verify that event ID 4657 appears in the Security event log and includes the expected old and new values.

If event ID 4657 does not appear in the Security event log after you modify a registry value under the MSCEP key, confirm that the Registry audit subcategory is enabled.

auditpol.exe /get /subcategory:"{0CCE921E-69AE-11D9-BED3-505054503030}"

If you deployed the Sysmon configuration, confirm it is loaded and generating events. Sysmon events are recorded in the Applications and Services Logs > Microsoft > Windows > Sysmon > Operational event log. The log should include events related to the test, including the registry value modification. Depending on how the application pool was recycled and which process-creation rules are enabled, it might also contain the process that initiated the recycle.

You will also find events containing process creation details, including the full command line, process ID, parent process ID, and related information.

Finally, perform a device enrollment. Certificate enrollment should remain unaffected by these changes, and confirming successful enrollment after making these changes is essential before returning the NDES server to production.

Restore the Previous Registry Permissions

If enrollment breaks and the cause is not immediately obvious, administrators can restore the security descriptor captured earlier by running the following PowerShell commands.

$Sddl = Get-Content -Path '.\mscep-acl-backup.txt' -Raw
$Acl = Get-Acl -Path $Key -Audit
$Acl.SetSecurityDescriptorSddlForm($Sddl.Trim())
Set-Acl -Path $Key -AclObject $Acl
Restart-WebAppPool -Name SCEP

In practice, the most common cause of failure is granting access to the wrong service identity. This is why confirming the application pool identity is the first step in this process. Administrators should not skip this validation step.

Summary

The MSCEP registry values determine which certificate templates NDES uses for SCEP enrollment. An attacker with administrative access to the NDES server could modify these values and redirect enrollment to an unintended template without creating an obvious service failure. Restricting access to the MSCEP key reduces unnecessary exposure, while registry auditing and Sysmon provide visibility into unauthorized changes and the processes responsible for them. Forward these events to your SIEM, configure alerts for unexpected modifications, and validate the detection workflow before relying on it in production.

Additional Information

Sample Sysmon Configuration for NDES on GitHub

Download Sysmon from Microsoft Sysinternals

Microsoft NDES Information Disclosure: Detection and Remediation

Get-NdesNtlmDisclosure PowerShell Script on GitHub

Configure Infrastructure to Support SCEP with Microsoft Intune

Publish NDES with Microsoft Entra Application Proxy

Microsoft NDES Information Disclosure: Detection and Remediation

The Active Directory Certificate Services (AD CS) Network Device Enrollment Service (NDES) is a common building block for certificate deployment with Microsoft Intune. When NDES is used with the Intune Certificate Connector, the NDES server is published to the Internet so that managed devices can enroll for certificates using the Simple Certificate Enrollment Protocol (SCEP). Anything accessible via the Internet warrants careful attention, and a default NDES installation can expose more information than administrators might expect. Specifically, the NDES administration page can disclose sensitive information and should be removed. However, removing access to the page isn’t enough. Even after the NDES administration page is removed, IIS can continue to expose Windows authentication on that path through orphaned configuration entries, enabling NTLM-based information disclosure to unauthenticated Internet clients.

NDES Administration Page

NDES exposes its web-based functionality through applications hosted in Internet Information Services (IIS). A default NDES installation creates two IIS applications under the CertSrv virtual directory. The first is mscep, which is the SCEP endpoint itself. The second is mscep_admin, which is the NDES administration page used to generate one-time challenge passwords.

Standalone Configuration

In a standalone NDES deployment, an administrator browses to the administration page, authenticates, and receives a one-time password that is embedded in the certificate request. NDES validates the password against its local cache before forwarding the request to the certification authority (CA).

Intune Certificate Connector

The Intune Certificate Connector does not use this mechanism. Intune generates its own challenge, and the NDES policy module installed by the connector validates the certificate request against the authorizations Intune has granted for that specific device. The connector also disables the standard NDES challenge-password mechanism. As a result, the administration page is not used for Intune certificate enrollment and serves no operational purpose in this configuration.

Preauthentication Limitations

Reverse-proxy preauthentication normally provides an additional security boundary by requiring a client to authenticate before its request is forwarded to the published application. With Microsoft Entra Application Proxy, Microsoft Entra ID preauthentication can block unauthenticated Internet clients from reaching the internal web application, reducing its exposure to scanning, password-spraying attacks, and other malicious requests.

However, SCEP clients cannot complete the Microsoft Entra ID authentication process or present the authentication token required by Application Proxy. Enabling preauthentication would therefore prevent managed endpoints from reaching NDES and enrolling for certificates. When publishing NDES through Microsoft Entra Application Proxy, the Pre Authentication setting must be configured as Passthrough. Other reverse proxies must similarly allow unauthenticated requests to reach the NDES SCEP endpoint. The Intune SCEP policy module, not the reverse proxy, validates and authorizes certificate requests before NDES submits them to the certification authority.

Information Disclosure

Because the NDES administration page is configured to use Windows authentication, IIS can negotiate NTLM with an unauthenticated client that requests the mscep_admin path. When the client sends an NTLM Type 1 negotiation message, IIS can respond with a Type 2 challenge containing a target information block. No credentials are required to receive this challenge or the information it contains.

Depending on the server configuration and negotiated NTLM options, the Type 2 message can disclose some or all of the following information:

  • NetBIOS domain name
  • NetBIOS computer name
  • DNS domain name
  • DNS computer name (server FQDN)
  • DNS forest name
  • Operating system version and build number

This is significant because the internal Active Directory namespace often differs from the public namespace used to publish NDES. For example, the published external name might be ndes1.example.com, but the NTLM challenge might disclose an internal domain of corp.example.net and a server FQDN of ndes1.corp.example.net. None of that information is available from public DNS.

Testing

To view disclosed information, use curl.exe to send a static NTLM type 1 negotiation message and inspect the response headers. Run the following command on the NDES server.

curl.exe -skI -H 'Authorization: NTLM TlRMTVNTUAABAAAAB4IIAAAAAAAAAAAAAAAAAAAAAAA=' https://localhost/certsrv/mscep_admin

A response containing a WWW-Authenticate header with an NTLM value indicates the endpoint is offering a challenge. When the header includes a base64 payload beginning with TlRMTVNTUAAC, the server has returned a type 2 message, leading to information disclosure on the target host. A response with no WWW-Authenticate header at all is the desired result.

Here are the PowerShell commands to decode and view the base64 payload and the disclosed information.

$Response = curl.exe -skI -H 'Authorization: NTLM TlRMTVNTUAABAAAAB4IIAAAAAAAAAAAAAAAAAAAAAAA=' https://localhost/certsrv/mscep_admin
$Challenge = ($Response | Select-String -Pattern '^WWW-Authenticate:\s*NTLM\s+(\S+)').Matches.Groups[1].Value
$Bytes = [Convert]::FromBase64String($Challenge)
[Text.Encoding]::Unicode.GetString($Bytes) -Replace '[^\x20-\x7E]', ' '

PowerShell Script

I have created and published a PowerShell script to simplify testing NDES servers for information leakage. The script is published on GitHub here. In addition, you can install the script from the PowerShell Gallery by running the following command.

Install-Script -Name Get-NdesNtlmDisclosure

The output of the command on a vulnerable server is as follows.

A Note on External Testing

When NDES is published using Microsoft Entra Application Proxy, external test results can be inconsistent. In my repeated testing across three separate servers, the first request sometimes returned a bare NTLM challenge with no payload, and a second request, seconds later, returned the full type 2 message. Therefore, do not treat a single clean external result as confirmation. Test locally on the server itself, then repeat external tests at least twice to confirm the results.

Additional Security Concerns

Beyond the namespace disclosure, an Internet-accessible NDES administration page introduces some additional security concerns.

Password Spray Attacks

An internet-facing endpoint that accepts domain credentials is a target for password spraying attacks. Failed authentication attempts can count toward the configured account-lockout threshold, introducing a potential denial-of-service risk to user accounts.

Service Disclosure

The presence of an NTLM challenge on the well-known mscep_admin path also identifies the server as an NDES host, providing attackers with useful reconnaissance information for targeted attacks.

Remediation

If the reverse proxy configuration exposes the NDES administration page, it becomes an Internet-accessible authenticated endpoint that no part of the Intune enrollment workflow uses. Removing it is a simple and effective attack-surface reduction measure.

Remove the NDES Administration Page

Administrators can remove the NDES administration page IIS application by opening an elevated PowerShell command window and running the following command.

Remove-WebApplication -Site 'Default Web Site' -Name 'CertSrv/mscep_admin'

After running this command, browsing to the administration page returns HTTP 404. The application is gone, and SCEP enrollment continues to work normally. At this point, most administrators would consider the task complete.

The Problem

If you attempt to browse the administration page after removing it, you will still be prompted to authenticate. If you supply valid credentials, you will receive the expected 404. The authentication prompt itself is the real problem.

IIS Authentication Settings

The NDES role configuration writes IIS authentication settings for the administration page into a separate location element in applicationHost.config. Remove-WebApplication deletes the application definition under the sites element, but it does not touch the location element. IIS continues to match the path and applies the authentication settings it finds there, even though no application exists at that location.

The orphaned configuration is visible only in the raw configuration file. It does not appear in IIS Manager, and Get-WebApplication reports nothing at that path. You can run the following command to view this configuration.

Select-String -Path "$env:SystemRoot\System32\inetsrv\config\applicationHost.config" -Pattern '<location path=|windowsAuthentication enabled='

On a server where the administration page has been removed, the output still includes an entry like the following.

991: <location path=”Default Web Site/CertSrv/mscep_admin”>
997: <windowsAuthentication enabled=”true”>

Orphaned Configuration

To fully remediate this information disclosure and prevent potential disruption caused by password-spraying attacks, administrators must also remove the orphaned configuration location. This eliminates Windows authentication on the administration path entirely.

Remove-WebConfigurationLocation -Name 'Default Web Site/CertSrv/mscep_admin'

The NDES role configuration also enables Windows authentication on the SCEP application. Because anonymous authentication is also enabled, requests to the SCEP endpoint are ordinarily processed without an authentication challenge. However, Windows authentication is not required on an NDES server supporting the Intune Certificate Connector, and leaving it enabled on an Internet-facing endpoint serves no operational purpose. I recommend disabling it explicitly.

Set-WebConfigurationProperty -PSPath 'MACHINE/WEBROOT/APPHOST' -Location 'Default Web Site/CertSrv/mscep' -Filter 'system.webServer/security/authentication/windowsAuthentication' -Name 'enabled' -Value $False

By default, Windows authentication is handled in kernel mode, so stale state information in HTTP.SYS can continue serving challenges after a configuration change. Be sure to run iisreset.exe after making these changes.

iisreset.exe /restart

Validation

Repeat the NTLM probes demonstrated earlier against the administration page. The absence of a WWW-Authenticate header confirms the challenge has been eliminated.

curl.exe -skI -H 'Authorization: NTLM TlRMTVNTUAABAAAAB4IIAAAAAAAAAAAAAAAAAAAAAAA=' https://localhost/certsrv/mscep_admin

Confirm that SCEP still responds anonymously. A status code of 200 with a plain-text capability list is expected.

curl.exe -skI 'https://localhost/certsrv/mscep/mscep.dll?operation=GetCACaps'

Repeat the first test against the internal FQDN and the published external FQDN, then perform a device enrollment to confirm the deployment is unaffected.

PowerShell

After making these changes, Get-NdesNtlmDisclosure.ps1 will indicate that the NTLM challenge is not offered.

Summary

The NDES administration page is not required when the Intune Certificate Connector is installed on an NDES server and should be removed as part of attack surface reduction. However, removing the IIS application leaves behind an orphaned configuration location that continues to apply Windows authentication settings to the path. The result can be an Internet-facing endpoint that discloses the internal domain name, server name, forest name, operating system build, and other information to an unauthenticated remote client that initiates NTLM negotiation.

Removing the admin application alone is not enough. You must also remove the configuration location, disable Windows authentication where it is not required, restart IIS, and validate the result with an NTLM probe to ensure full mitigation.

Additional Information

Get-NdesNtlmDisclosure PowerShell Script on GitHub

Publish NDES with Microsoft Entra Application Proxy

Intune Certificate Connector Configuration Failed

Microsoft Intune Certificate Connector Failure

Certificate Connector for Intune Configuration Failure

Create and Assign SCEP Profiles in Microsoft Intune

RFC 8894 – Simple Certificate Enrolment Protocol

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

The Myth of the Publish Certificate in Active Directory Setting

Certificate templates in Microsoft Active Directory Certificate Services (AD CS) provide powerful, preconfigured settings that enable administrators to issue certificates tailored for specific purposes. For example, a certificate template could allow a user to authenticate to a Wi-Fi network or VPN gateway. Another template might control policies for enrolling for web server certificates in the enterprise. Templates define settings such as cryptographic parameters (key algorithm and length), validity period, application policies, enrollment requirements, and more. While there are myriad settings to choose from, one in particular is often enabled unnecessarily. And while it works without issue, there can be some hidden downsides to enabling this setting.

Publish Certificate in Active Directory

When creating a certificate template, there’s an option on the General tab called Publish certificate in Active Directory. From experience, this is one of the most misunderstood settings for certificate templates.

Intuitively, it would make sense to check this box on all published certificate templates. After all, I want the users or devices targeted by this certificate template to find them in Active Directory (AD) so they can enroll. Many administrators believe that enabling this setting is required to ‘see’ the published certificate template on the endpoint, as shown here.

However, enabling the Publish certificate in Active Directory option is not required for enrollment. To ‘see’ certificates available for enrollment, the user or device must only have the Enroll permission on the template.

What Is It For?

So, what does the Publish certificate in Active Directory setting do? When this option is enabled, the issuing CA adds the certificate to the requesting principal’s Active Directory account. There are two common scenarios where this is required.

S/MIME

Adding a user’s certificate to their AD account makes the public key centrally discoverable, allowing Outlook and other S/MIME-enabled clients to automatically find recipients’ certificates for secure email encryption and signature validation. Without the certificate published in AD, users must manually exchange certificates, breaking seamless S/MIME encryption in most enterprise environments.

Encrypting File System (EFS)

Publishing a user’s EFS certificate to their Active Directory account allows Windows to locate the correct public key automatically when encrypting files. It ensures recovery agents and key archival processes function properly. Without the certificate in AD, EFS can fail to encrypt data consistently across machines or prevent access to encrypted files when users roam or recover profiles.

Drawbacks

There are very few scenarios outside of S/MIME and EFS that require the Publish certificate in Active Directory option to be enabled. However, enabling it doesn’t necessarily break anything, and this setting is often enabled by default (or carried over from the source template when duplicating), so administrators may miss this option. Issuing certificates in this way introduces some potential problems.

AD Database Bloat

Adding a certificate to each principal’s AD object increases the size of each object, thereby increasing the total size of the AD database. For organizations with large directories with hundreds of thousands or even millions of accounts, adding unnecessary data to each account can be very expensive in terms of database size, replication traffic, backup storage, and overall domain performance. Making matters worse, certificates published to AD live perpetually. They are not removed automatically when certificates are revoked or expire.

Service Accounts

Service accounts used for certificate enrollment, such as the Microsoft Intune Certificate connector, can be especially challenging. Here, if the Publish certificate in Active Directory setting is enabled on the Intune certificate template, the CA will add a certificate to the service account for every certificate it issues. While you can have many certificates associated with a single account, there is an upper limit, approximately 1250, based on my testing. After that, certificates will continue to be issued, but adding them to AD will fail.

Remediation

The following recommendations can help administrators correct this misconfiguration and limit its impact in their environment.

Disable Unnecessary Certificate Publishing

Administrators should clear the Publish certificate in Active Directory setting on all certificate templates that do not explicitly require it, such as those used for S/MIME or Encrypting File System (EFS). This prevents new certificates from being written to user or computer objects and does not require certificates to be reissued.

Remove Published Certificates

Administrators can remove unnecessary certificates from user, computer, and service account objects in AD to reduce object and overall AD database sizes. Perform the following steps to remove unneeded certificates.

  1. Open the Active Directory Users and Computers management console (dsa.msc) and double-click the target principal.
  2. Select the Published Certificates tab.
  3. Select a certificate (or all certificates) and click Remove.

Important Note: Use extreme caution when deleting certificates! Do not delete any certificates unless you are certain they are not required.

Managed Service Accounts

Managed Service Accounts in AD do not have a Published Certificates tab. Administrators can use the Attribute Editor to remove individual certificates from the userCertificate attribute on the account.

Managed Service Account Attribute Editor

Managed Service Account userCertificate Entries

Unfortunately, there is no option to view the certificate in the UI for Managed Service Accounts. To view detailed certificate information, see the PowerShell section below.

Existing Certificates Are Not Removed Automatically

Disabling the Publish certificate in Active Directory setting only stops future certificates from being published in AD. Certificates already written to Active Directory are never removed automatically, even after they expire or are revoked. In environments where this setting has been enabled for an extended period, large numbers of stale certificates often accumulate and continue to increase the AD database size.

Intune Certificate Connector Considerations

This issue is especially problematic for high-volume enrollment scenarios that use service accounts, such as the Microsoft Intune Certificate Connector. When publishing is enabled for Intune certificate templates, certificates issued on behalf of users are added to the service account, quickly leading to excessive certificate accumulation and potential attribute limits.

ADPrincipalCertificate PowerShell Module

Manually performing this cleanup at scale is impractical. To assist administrators with cleaning up unnecessarily published certificates, I’ve created the ADPrincipalCertificate PowerShell module. This module includes functions to enumerate AD accounts that include certificates, show and optionally export certificates for AD accounts, and remove published certificates. The module also includes a function to enumerate published certificate templates that include the Publish certificate in Active Directory option enabled. You can install the ADPrincipalCertificate PowerShell module from the PowerShell gallery by running the following command.

Install-Module -Name ADPrincipalCertificate -Scope CurrentUser

See the ADPrincipalCertificate GitHub repository for detailed usage information.

Summary

While the Publish certificate in Active Directory option is helpful for S/MIME and EFS deployments, it is unnecessary for most other scenarios and is often enabled when it isn’t needed. This results in the unnecessary addition of certificates to AD accounts, causing individual objects and the entire AD database to grow without benefit. Sadly, many vendor guides indicate that this setting is required when it often isn’t, so many environments suffer from this misconfiguration. Administrators should review the certificate template configuration and disable this setting when it isn’t needed. Additionally, use the ADPrincipalCertificate PowerShell module to perform cleanup, if required.

Additional Information

ADPrincipalCertificate PowerShell Module on GitHub

ADPrincipalCertificate PowerShell Module in the PowerShell Gallery

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

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