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

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

Mastering Certificates with Microsoft Intune September 2026

I’m excited to announce that I will be delivering another edition of the Mastering Certificates with Microsoft Intune course, hosted by ViaMonstra Online Academy. This is a three-day live online training course that takes place September 1-3, 2026. This course dives deep into issuing and managing certificates using Microsoft Intune, covering both on-premises and cloud-based solutions.

Course Overview

This interactive training equips IT professionals with the skills to provision and manage enterprise PKI certificates using Microsoft Intune. It explores Active Directory Certificate Services (AD CS), Microsoft Cloud PKI for Intune, and non-Microsoft solutions, with live demonstrations featuring real-world scenarios.

Key Learning Objectives

Those taking the online training course will learn the following.

  • Certificate Basics: Understand certificate roles and enterprise use cases.
  • Deployment Options: Master Intune certificate deployment (Intune policies, revocation, security) and Microsoft Cloud PKI (licensing, benefits, limitations, BYOCA).
  • Intune Deployment: Learn PKCS and SCEP deployment, security best practices, and troubleshooting.
  • High Availability: Explore strategies for reliable certificate management.

Course Highlights

Here are some key highlights for attendees of the training.

  • Expert-Led: Learn from a veteran IT professional, a Microsoft MVP, with deep PKI and Intune expertise.
  • Interactive Demonstrations: The course includes numerous practical exercises in real-world scenarios.
  • Resources: Access to security best practices and sample scripts for automated configuration.
  • Community: Join a private Facebook group for peer collaboration.
  • Live Q&A: Engage directly with the instructor for a clearer understanding.

Who Should Attend?

This training event is ideal for IT administrators, security professionals, and systems engineers working with Intune, AD CS, or Microsoft Cloud PKI for Intune.

Prerequisites

Those attending the online training course should be familiar with the following.

  • Basic networking knowledge (TCP/IP, DNS).
  • Familiarity with Active Directory, Windows OS, and Intune.
  • Access to an AD CS setup and an Azure subscription with Intune Suite licenses.

Why It Matters

Certificates are vital for secure authentication and communication. This course bridges theory and practice, equipping you to deploy and manage digital certificates effectively in cloud-native environments.

Details

Here is some additional information about the training event.

  • When: September 1-3, 2026 (sessions begin at 9:00 AM CDT).
  • Where: Live online via ViaMonstra Online Academy.
  • Cost: $2,395.00 (Sold separately – not included in All-Access Pass).

Why ViaMonstra?

ViaMonstra delivers top-tier IT training from Microsoft MVPs, focusing on practical, up-to-date skills and fostering a collaborative community.

Take the Next Step

Ready to master certificate management with Microsoft Intune? Register at ViaMonstra Online Academy for the August 2025 Mastering Certificates with Microsoft Intune training course today!

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

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

With Windows Server 2016 fast approaching end of life (EOL – January 2027) I’ve been helping many customers get their existing Network Device Enrollment Service (NDES) server upgraded to Windows Server 2025. In the past I’ve had few problems deploying NDES on Windows Server 2016, 2019, and 2022. However, NDES deployments on Windows Server 2025 have proven more challenging. Unlike previous releases, many installations fail during initial configuration with little indication of the underlying cause. The error described below is quite common, in my experience.

Unsupported Cert Type

When configuring the NDES role on Windows Server 2025, administrators may encounter an installation failure with the following error message.

Failed to enroll RA certificates. The requested certificate template is not supported by this CA. 0x80094800 (-2146875392 CERTSRV_E_UNSUPPORTED_CERT_TYPE)

Investigation

Inspection of the issuing CA confirmed that the required NDES certificate templates had been published successfully and were visible on the target issuing CA server.

After confirming the templates were published, I validated connectivity between the NDEs server and the issuing CA to rule out communication issues.

certutil.exe -config <servername\commonname> -ping

Root Cause

Although the precise root cause remains unclear, the issue appears related to timing or object availability during NDES configuration. In many cases it behaves like a delay in template publication visibility, Active Directory replication latency, or another dependency timing issue encountered during setup.

Note: This error can also occur if the administrator is not a member of the Enterprise Administrators group, or if the security permissions on these default templates has changed.

Recovery

Fortunately, if you encounter this issue you can usually just remove the configuration using PowerShell and run it again.

Uninstall-AdccsNetworkDeviceEnrollmentService -Force

However, in my experience running the installer again results in another error, usually the 0x80070003 ‘Path Not Found’ error. If that happens, see my published guidance for recovering from this error here.

https://directaccess.richardhicks.com/2026/05/26/troubleshooting-ndes-error-0x80070003-path-not-found-on-windows-server-2025

While recovery is usually straightforward, preventing the issue entirely is preferable.

Recommendation

I recommend publishing the required templates on the target issuing CA before proceeding with the NDES configuration. Publishing these templates manually before running NDES configuration ensures they are already visible and available to the CA, potentially avoiding timing-related enrollment failures during setup. The following default templates are required for NDES configuration.

  • IPsec (Offline request)
  • CEP Encryption
  • Exchange Enrollment Agent (Offline request)

Note: Best practice is to remove these templates after configuration because they are intended only for NDES registration authority enrollment and are not typically required for ongoing issuance.

Summary

When deploying NDES on Windows Server 2025, administrators may encounter the 0x80094800 CERTSRV_E_UNSUPPORTED_CERT_TYPE error even when the required templates appear correctly configured. Although the exact cause remains uncertain, the issue appears related to timing or template availability during setup. In most cases, removing and re-running the NDES configuration resolves the problem, while pre-publishing the default NDES templates before configuration can help prevent it entirely.

Additional Information

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

Intune PKCS and SCEP Certificate Validity Period

TRAINING: Mastering Enterprise PKI Certificates with Microsoft Intune

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

When deploying enterprise PKI certificates with Microsoft Intune using SCEP, administrators must deploy one or more on-premises Network Device Enrollment Service (NDES) servers together with the Intune Certificate Connector. Installing and configuring NDES can be challenging because the solution includes multiple dependencies and has many moving parts. Troubleshooting installation failures can be difficult, particularly on Windows Server 2025 where I have observed installation issues more frequently than on earlier Windows Server releases.

Path Not Found

As I work with customers to migrate their existing NDES services to Windows Server 2025, I frequently encounter installation errors. Specifically, the ‘Path Not Found’ error is increasingly common. Using PowerShell or the Server Manager, administrators may encounter a failed NDES installation that returns the following error message.

CMSCEPSetup::Install: The system cannot find the path specified. 0x80070003 (WIN32: 3 ERROR_PATH_NOT_FOUND)

Investigation

Reviewing the NDES installation log at C:\Windows\certocm.log yields an important clue.

Microsoft Active Directory Certificate Services: Failed to add the web virtual directory. The system cannot find the path specified. 0x80070003 (WIN32: 3 ERROR_PATH_NOT_FOUND): The system cannot find the path specified. 0x80070003 (WIN32: 3 ERROR_PATH_NOT_FOUND)

Root Cause

This error occurs after a failed installation attempt which corrupts the IIS configuration on the NDES server. This prevents the NDES installer from configuring applications in the default web site. Fortunately, the problem is easy to resolve.

Recovery Steps

To recover from this error, first uninstall the NDES service (not the role) by opening an elevated PowerShell command window and running the following command.

Uninstall-AdcsNetworkDeviceEnrollmentService -Force

Next, remove the corrupt IIS configuration file.

Remove-Item C:\Windows\System32\inetsrv\config\applicationHost.config -Force

Copy a known-good IIS configuration file from the WinSxS folder.

$WinSxSConfig = Get-ChildItem C:\Windows\WinSxS -Recurse -Filter applicationHost.config -ErrorAction SilentlyContinue | Sort-Object LastWriteTime -Descending | Select-Object -First 1
Copy-Item -Path $WinSxSConfig.FullName "C:\Windows\System32\inetsrv\config\applicationHost.config" -Force

And finally, recreate the default website.

& "$env:SystemRoot\System32\inetsrv\appcmd.exe" add site /name:"Default Web Site" /bindings:http/*:80: /physicalPath:"%SystemDrive%\inetpub\wwwroot"

Once complete, proceed with the NDES configuration.

Pro Tip

Because this issue occurs frequently enough in my experience, I recommend backing up the IIS configuration immediately after installing the NDES role and before beginning configuration. You can backup the IIS configuration by opening an elevated PowerShell command window and running the following command.

& "$env:SystemRoot\System32\inetsrv\appcmd.exe" add backup 'Backup Name'

If the NDES configuration subsequently fails, uninstall the configuration, then restore the backup using the following command.

& "$env:SystemRoot\System32\inetsrv\appcmd.exe" restore backup 'Backup Name'

Once complete, proceed with the NDES configuration once again.

Summary

NDES installation failures on Windows Server 2025 can leave IIS in an inconsistent state and trigger 0x80070003 ERROR_PATH_NOT_FOUND errors during configuration. Restoring a known-good IIS configuration and recreating the default web site resolves the issue quickly. Backing up the IIS configuration before beginning NDES configuration can significantly reduce recovery time if installation problems occur.

Additional Information

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

Intune PKCS and SCEP Certificate Validity Period

TRAINING: Mastering Enterprise PKI Certificates with Microsoft Intune

Microsoft AD CS Adds Post-Quantum Cryptography Support with ML-DSA

Despite predictions of its decline, Microsoft Active Directory Certificate Services (AD CS) continues to evolve. Following significant enhancements introduced in late 2025, including CRL partitioning and support for 16K database pages, the May 2026 update adds another important capability: support for Post-Quantum Cryptography (PQC).

ML-DSA

Specifically, the May 2026 update adds support for ML-DSA-44, ML-DSA-65, and ML-DSA-87 in Windows Server 2025 for AD CS. This enables administrators to begin evaluating post-quantum cryptographic algorithms and assessing PQC readiness in enterprise PKI environments

Configuration

After applying the May 2026 update to an issuing Certification Authority (CA), administrators will find new PQC algorithms under the Algorithm name drop-down list, as shown here.

Note: If you don’t see these new algorithms, ensure you have selected Key Storage Provider from the Provider Category drop-down list. In addition, ensure that you select Signature on the Request Handling tab.

Test Results

Initial testing across common enterprise certificate scenarios produced mixed results. While PQC works well in some scenarios, other workloads still show limitations.

Code Signing

Code signing with an ML-DSA-44 certificate issued by AD CS works perfectly. For example, I can use Set-AuthenticodeSignature to sign a PowerShell script, as shown here.

Viewing the file’s properties shows that the encryption algorithm used to sign the file was ML-DSA-44, as expected.

IIS

TLS-based workloads proved more challenging. Attempts to configure an HTTPS binding in IIS failed with the following error message.

There was an error while performing this operation. A specified logon session does not exist. It may already have been terminated. (Exception from HRESULT: 0x80070520).

RRAS and SSTP

Similar limitations occurred when testing remote-access VPN scenarios using RRAS and SSTP. Specifically, configuring a PQC TLS certificate for SSTP in RRAS failed. Although I was able to assign the certificate using Set-RemoteAccess, the RemoteAccess service failed to start.

Remote Desktop

Unfortunately, using PQC certificates for RDP also fails. Although I could assign the PQC certificate to the RDP listener, clients fail to connect using RDP and return the following error message.

This computer can’t connect to the remote computer. Try connecting again. If the problem continues, contact the owner of the remote computer or your network administrator.

Error code: 0x904
Extended error code: 0x7

Summary

The May 2026 update marks an important milestone for AD CS by introducing initial support for PQC algorithms, allowing organizations to begin evaluating ML-DSA certificates in enterprise environments. Early testing shows promising results for signing scenarios such as code signing; however, broader infrastructure workloads, including TLS, VPN, and Remote Desktop, remain limited today. Although PQC support is still in its early stages, these updates demonstrate Microsoft’s ongoing investment in AD CS and provide administrators with an opportunity to begin preparing their PKI environments for the post-quantum future. Additional PQC enhancements, including ML-KEM support and broader ecosystem integration, are anticipated in future Windows updates.

Additional Information

Microsoft May 2026 Security Updates (KB5087539)

Post Quantum Cryptography in the Enterprise

The Case for 6-Day Public TLS Certificates

In February 2025, Let’s Encrypt introduced the option to enroll for public TLS certificates with a 6-day validity period.  This represents a significant shift toward short-lived certificates and aligns with the broader industry trend of reducing certificate lifetimes to improve security. While this may seem aggressive at first glance, organizations that have embraced automation will find that extremely short-lived certificates offer compelling security and operational advantages in some scenarios.

Benefits

Extremely short-lived TLS certificates offer several important security and operational benefits, particularly for organizations that have already embraced automation for certificate lifecycle management. Key advantages include:

  • Minimized Risk of Key Compromise – 6-day certificates dramatically reduce the exposure window of private key compromise events, giving attackers a limited window of opportunity to exploit key access.
  • Automation Validation – Short-lived certificates force organizations to adopt and validate automated enrollment and renewal processes, ensuring that certificate lifecycle management is reliable and resilient.
  • IP Address Support – 6-day TLS certificates from Let’s Encrypt support IP addresses, allowing administrators to secure workloads that do not have entries in DNS.

Use Cases

6-day TLS certificates are well-suited for a range of modern workloads, especially those that benefit from frequent key rotation, automation, and dynamic provisioning. 6-Day TLS certificates are well-suited for the following workloads:

  • High Value Resources – Using 6-day TLS certificates is beneficial for high-security or sensitive workloads where frequent key rotation is desired.
  • Test Labs – High-frequency certificate rotation allows for thorough testing of automation processes to ensure operational reliability of production deployments. Rapid iteration of 6-day TLS certificates allows administrators to identify potential issues and implement changes before long-term certificates expire.
  • Ephemeral Infrastructure – 6-day TLS certificates work well with dynamic workloads such as containers, where environments are rapidly provisioned and destroyed. These hosts might only live for a few hours or days, making short-lived certificates an ideal choice in this scenario.
  • Workload Bootstrapping – 6-day TLS certificates can be used where a certificate is required only to perform initial configuration. For example, an IP-based TLS certificate can be used to configure TLS services, then later migrated to a long-term certificate when DNS is configured and the service is placed into production.

Enterprise Usage

Administrators will find that 6-day public TLS certificates work well with many popular Windows Server workloads. Here are a few examples.

  • Always On VPN – Enterprise secure remote access is a popular target for attackers because the service is exposed to the Internet. Using 6-day TLS certificates ensures frequent key rotation, reducing exposure to key compromise.
  • Remote Desktop Services – Many organizations continue to use Remote Desktop Gateway to provide access to on-premises applications, another workload that is exposed to the Internet. Using 6-day TLS certificates is equally effective in this scenario.

What About DirectAccess?

Although DirectAccess would be another ideal Windows Server workload for 6-day TLS certificates, my testing shows that it does not work. The root cause is that 6-day TLS certificates from Let’s Encrypt do NOT include subject information (the field is blank). Unfortunately, because of the way in which DirectAccess validates this certificate, it requires information in this field. More details can be found here.

https://directaccess.richardhicks.com/2026/03/16/directaccess-iphttps-and-lets-encrypt-6-day-certificates/

Summary

If you are automating certificate enrollment and renewal, it shouldn’t matter if the certificate is valid for 6 days or 60 days. In fact, shorter lifetimes can significantly improve your security posture by minimizing risk and enforcing operational discipline around certificate management. Organizations that invest in automation today will be well-positioned to adopt even shorter certificate lifetimes in the future, while those relying on manual processes will find it increasingly difficult to keep up.

Questions?

Do you have questions about certificate lifecycle automation in your environment? I’m happy to help you validate your approach and address any challenges you’re encountering. Fill out the form below, and I’ll provide you with more information.

Additional Information

Let’s Encrypt Issues First Six-Day Certificate

DirectAccess IP-HTTPS and Let’s Encrypt 6-Day TLS Certificates

The Case for Short-Lived Certificates in the Enterprise

DirectAccess IPHTTPS and Let’s Encrypt 6-Day Certificates

I’ve written extensively about how public TLS certificate lifetimes will drop to just 47 days by March 2029. Before then, we’ll see certificate lifetimes gradually drop from the current 398 days to 200 days on March 15, 2026, and then to 100 days on March 15, 2027. In preparation for this, I’ve been working with many customers to deploy automated certificate enrollment and renewal solutions to eliminate the need for manual intervention. Interestingly, Let’s Encrypt now offers extremely short-lived certificates that are good for just 6 days! While they work just fine for Always On VPN, I discovered they will not work for DirectAccess.

6-Day Certificate

After successfully enrolling for a 6-day TLS certificate from Let’s Encrypt (I used CertKit, BTW!), I encountered an error when trying to assign the short-lived certificate to the IP-HTTPS listener in the DirectAccess configuration. Specifically, when running the Set-RemoteAccess PowerShell command, I received the following error.

Set-RemoteAccess: The parameter is incorrect.

Further investigation showed that I could install other public TLS certificates just fine. For some reason, though, DirectAccess did not like this new 6-day certificate.

Missing Subject Name

After digging a bit deeper, I realized the Subject field of the new 6-day Let’s Encrypt certificate was empty.

Subject vs. SAN in Modern TLS

Modern TLS clients rely entirely on the Subject Alternative Name (SAN) field for identity validation, and the older practice of matching against the certificate’s Subject field has been phased out for many years. Many certificate authorities, including Let’s Encrypt, now leave the Subject field empty because it no longer serves a functional purpose in current TLS implementations. DirectAccess still expects this field to contain data and does not properly fall back to SAN‑only validation. As a result, any certificate with an empty Subject field, such as the new 6‑day certificates from Let’s Encrypt, will fail when applied to the DirectAccess IP‑HTTPS listener.

Workaround

Admittedly, using 6-Day public TLS certificates for DirectAccess is extreme and likely overkill for this workload. The good news is that DirectAccess still works perfectly with 90-day Let’s Encrypt certificates, so the lack of 6-day certificate support should not be impactful.

CertKit

Have you heard about CertKit? CertKit, an online service for automating Let’s Encrypt certificate enrollment and renewal, has added support for Always On VPN and DirectAccess. Find details on leveraging it for public TLS certificates for these solutions here.

Additional Information

Always On VPN SSTP with Let’s Encrypt Certificates

Always On VPN and 47-Day Public TLS Certificates

The Case for Short-Lived Certificates in Enterprise Environments

CertKit Agent Support for Always On VPN SSTP and DirectAccess IP-HTTPS TLS Certificates

CertKit Agent Support for Always On VPN SSTP and DirectAccess IP-HTTPS TLS Certificates

With public TLS certificate lifetimes set to drop to 200 days soon (next week!), Always On VPN and DirectAccess administrators face an increased risk of service disruption if certificates aren’t renewed on time. These shorter certificate lifetimes require more frequent renewals, substantially increasing management overhead. Although 200 days equate to roughly a twice-a-year renewal, lifetimes will decrease further to 100 days next year and eventually to just 47 days in 2029. SSTP and IP-HTTPS are TLS-based tunneling protocols used by Always On VPN and DirectAccess, respectively, tying their certificate health directly to remote access availability. Now is the time to automate the enrollment and renewal of Always On VPN SSTP and DirectAccess IP-HTTPS/TLS certificates to ensure reliable operation in the future.

Always On VPN

Previously, I wrote about using CertKit.io to automate the enrollment and renewal of public TLS certificates for Always On VPN. CertKit is an online service that administrators can use to delegate the task of enrolling for short-lived certificates from Let’s Encrypt. In that post, I shared some sample code to retrieve the certificate from CertKit and assign it to the SSTP listener for the Routing and Remote Access Service (RRAS). However, CertKit added new features to its solution, eliminating the need for additional code.

CertKit Agents

Recently, CertKit introduced CertKit Agents. These lightweight software agents are installed on Windows Servers (other operating systems are supported as well) to automate the process of downloading CertKit certificates and installing them in the local computer certificate store. Importantly, they now specifically support both the Always On VPN (SSTP) and DirectAccess (IP-HTTPS) workloads natively.

Always On VPN

The CertKit agent automatically detects the Routing and Remote Access (RRAS) workload and updates the certificate binding for the SSTP listener accordingly. Since this process requires a service restart, which terminates all current VPN connections, CertKit allows you to select an outage window for certificate updates.

Here, administrators can define the day(s) and time window during which the agent is authorized to restart the RemoteAccess service when updating the TLS certificate for SSTP. The day and time are based on the server’s configured time zone settings.

DirectAccess

Beginning with CertKit agent v1.6.2, the agent automatically detects whether DirectAccess is configured, enabling IP-HTTPS TLS certificates to be automatically enrolled and renewed. However, additional configuration is required. The following changes must be made to support CertKit for DirectAccess.

  • Service Account – Administrators must configure a service account in Active Directory for the CertKit agent. A Group Managed Service Account (gMSA) is preferred, but a standard domain service account is also supported.
  • GPO Delegation – CertKit service account must be delegated the ‘Edit settings, delete, and modify security’ permission on the DirectAccess server and client settings GPOs.
  • Log On as a Service – When using a domain service account, administrators must grant the CertKit service the ‘Log on as a service’ right on the DirectAccess server. However, when using gMSA, the ‘Log on as a service’ right is not required.
  • Local Administrator – Administrators must also add the CertKit agent service account to the Local Administrators group on the server.

Configuration Script

I have published a PowerShell script to simplify configuring the CertKit agent on DirectAccess servers. The script automatically performs all required tasks for the CertKit agent to work with DirectAccess. You will find the Enable-DACertKit.ps1 PowerShell script on GitHub. Alternatively, you can install the script directly from the PowerShell Gallery.

Install-Script -Name Enable-DACertKit -Scope CurrentUser

After installing the CertKit agent, run the PowerShell script to complete the configuration. Next, authorize the agent in the CertKit management portal and assign a certificate. Once complete, CertKit can fully manage the IP-HTTPS TLS certificate for DirectAccess.

Note: Like Always On VPN, changes to the DirectAccess IP-HTTPS certificate require a service restart, which is disruptive. Be sure to define a maintenance window (as shown previously) to ensure the change is made during non-peak times.

Summary

As TLS certificate lifecycles continue to shrink, automating certificate enrollment and renewal has become essential for both Always On VPN and DirectAccess environments. CertKit agents streamline this process by automatically retrieving, installing, and binding certificates for SSTP and IP-HTTPS, all while supporting scheduled outage windows to minimize disruption. With these new capabilities, administrators can significantly reduce operational overhead and ensure consistent, reliable remote access services without manual intervention. Visit CertKit.io to get started today.

More Information

If you would like to learn more about CertKit or see a demonstration with Always On VPN or DirectAccess, fill out the form below, and I’ll provide you with more details.

Additional Information

Always On VPN SSTP Certificate Automation with CertKit

CertKit Agents

Enable-DACertKit.ps1 on GitHub

Enable Group Managed Service Accounts