How to Identify Applications That Use Windows CLAT (WinCLAT) with Sysmon

Windows CLAT (WinCLAT) allows applications that use IPv4 sockets or literal IPv4 addresses to continue working on IPv6-only and IPv6-mostly networks by translating their IPv4 traffic to IPv6 for delivery to a NAT64 gateway. For administrators planning an IPv6-only deployment, this raises an obvious question: which applications still depend on IPv4 and are using WinCLAT?

Application Visibility

WinCLAT’s built-in logging does not identify the applications using it. This post explains how to use Microsoft Sysinternals Sysmon to record the executable, user account, and destination associated with IPv4 connections that use the WinCLAT source address. It also describes the filtering requirements and limitations of this approach. The behavior described applies to Sysmon 15.22. Later versions may differ.

What WinCLAT Logs

WinCLAT records events in the Microsoft-Windows-IPxlatCfg/Operational event log, but those events describe the WinCLAT instance on each interface, not the traffic passing through it.

Event IDDescription
1106Instance enabled
1107Instance disabled
1108Remote prefix discovered
1109Translation started
1110Translation stopped
1111WinCLAT IPv6 address DAD failure

No event identifies the application that used WinCLAT or the destination it connected to. The netsh.exe interface clat commands report the same kind of instance and configuration state. As a result, WinCLAT can translate traffic on an interface with no built-in record of what generated it.

Logging WinCLAT Connections with Sysmon

Sysmon is a Microsoft Sysinternals tool that runs as a Windows service and logs detailed system activity, including process creation, network connections, and file changes, to the Windows Event Log. Sysmon can be configured specifically to log network traffic generated by WinCLAT.

Identifying WinCLAT Traffic in Event ID 3

Sysmon Event ID 3 (Network connection) logs TCP and UDP connections and links each one to a process. When an application uses WinCLAT, its socket is still an IPv4 socket, so the event shows the application’s IPv4 addresses rather than the translated IPv6 addresses:

  • Calling executable and account – Image, ProcessId, ProcessGuid, and User
  • Destination – DestinationIp, DestinationPort, and Protocol
  • WinCLAT source address – SourceIp

The source address is what makes this useful. While WinCLAT is active, it assigns the interface an IPv4 address from the IPv4 Service Continuity Prefix 192.0.0.0/29 (RFC 7335), typically 192.0.0.1. Filtering on that source separates traffic that uses WinCLAT from other network activity. Traffic that uses a native IPv4 route has a different source address, and traffic from applications that use IPv6 directly, including through DNS64 and NAT64, is not IPv4 traffic and does not match.

Preparing the WinCLAT Filter

Network connection events are disabled by default, so Sysmon requires a configuration file to enable them. Save the following as sysmon-winclat.xml, or download it from GitHub here.

<Sysmon schemaversion="4.82">
  <DnsLookup>False</DnsLookup>
  <EventFiltering>
    <NetworkConnect onmatch="include">
      <SourceIp condition="is any">192.0.0.1;192.0.0.2;192.0.0.3;192.0.0.4;192.0.0.5;192.0.0.6;192.0.0.7</SourceIp>
    </NetworkConnect>
    <NetworkConnect onmatch="exclude">
      <DestinationIp condition="begin with">224.</DestinationIp>
      <DestinationIp condition="begin with">239.</DestinationIp>
      <DestinationIp condition="is">255.255.255.255</DestinationIp>
      <DestinationIp condition="is any">192.0.0.0;192.0.0.1;192.0.0.2;192.0.0.3;192.0.0.4;192.0.0.5;192.0.0.6;192.0.0.7</DestinationIp>
    </NetworkConnect>
    <ProcessCreate onmatch="include" />
    <FileCreateTime onmatch="include" />
    <ProcessTerminate onmatch="include" />
    <DriverLoad onmatch="include" />
    <RawAccessRead onmatch="include" />
  </EventFiltering>
</Sysmon>

The configuration does the following.

  • Includes connections with a source address in the WinCLAT range. A computer with several translating interfaces uses a different address on each one.
  • Excludes multicast and broadcast destinations, and destinations in the WinCLAT range itself. Local protocols such as LLMNR and NetBIOS can use the WinCLAT IPv4 address, but this traffic is not destined for NAT64. A source address in the WinCLAT range therefore does not by itself prove that a packet was translated.
  • Disables reverse DNS lookups with DnsLookup. A reverse lookup would add unnecessary queries, and its result would not show the name the application requested anyway.
  • Turns off other default event types with empty include rules. Without these rules, Sysmon also logs events such as process creation and termination, which are unrelated to WinCLAT and can far outnumber the network connection events. Sysmon still logs its service state and configuration change events, which cannot be filtered.

Turning off process creation events removes the command line and parent process from the log. To keep that context for investigations, remove the ProcessCreate rule and accept the additional volume. See the Sysmon documentation for more filtering options.

Installing and Configuring Sysmon

Sysmon is available natively in Windows 11 since February, 2026, but it is not installed by default. Administrators can install it by navigating to Settings > System > Optional features > More Windows features and selecting Sysmon.

Optionally, administrators can install Sysmon by opening an elevated PowerShell command window and running the following command.

Enable-WindowsOptionalFeature -Online -FeatureName Sysmon

For Windows versions that don’t include Sysmon, administrators can download Sysmon from the Sysinternals website.

Applying the WinCLAT Filter

After installing Sysmon, open an elevated command window and install it with the configuration file by running the following command.

sysmon.exe -i sysmon-winclat.xml

To apply a changed configuration to a computer where Sysmon is already installed, use -c.

sysmon.exe -c sysmon-winclat.xml

Reading Sysmon Events

Events are recorded in the Microsoft-Windows-Sysmon/Operational log.

Sysmon event log indicating the calling application.

Sysmon event log indicating the source and destination IPv4 addresses used by the calling application.

Viewing Recent Events with PowerShell

Run the following command to display the time and message for up to 20 of the most recent Sysmon Event ID 3 records.

Get-WinEvent -FilterHashtable @{ LogName = 'Microsoft-Windows-Sysmon/Operational'; Id = 3 } -MaxEvents 20 | Format-List -Property TimeCreated, Message

Sysmon event log details viewed using PowerShell.

The example above shows several fields of interest for a TCP connection to an IPv4 address through WinCLAT.

Network connection detected:
ProcessId: 10536
Image: C:\Tools\putty.exe
User: LAB\rhicks
Protocol: tcp
Initiated: true
SourceIsIpv6: false
SourceIp: 192.0.0.1
SourcePort: 50935
DestinationIsIpv6: false
DestinationIp: 172.16.0.254
DestinationPort: 22

Listing Applications and User Accounts

To produce a list of the applications and destinations recorded on a computer, read the values from the event data and remove the duplicates.

Get-WinEvent -FilterHashtable @{ LogName = 'Microsoft-Windows-Sysmon/Operational'; Id = 3 } |
    Select-Object -Property @{ Name = 'Image'; Expression = { $_.Properties[4].Value } },
        @{ Name = 'User'; Expression = { $_.Properties[5].Value } } |
    Sort-Object -Property Image, User -Unique |
    Format-Table -AutoSize

This query includes all retained Event ID 3 records, including events collected before the WinCLAT configuration was applied.

Unique application and user account combinations recorded by Sysmon.

To report across many computers, collect the events centrally with Windows Event Forwarding or a SIEM agent.

Interpreting the Results

Sysmon Event ID 3 records different information depending on the protocol and whether the connection succeeds. The table below shows which types of traffic can produce an event and what each record tells you about the connection.

Traffic through WinCLATRecorded by Event ID 3What an event means
TCP connectionYesThe connection was established
TCP attempt with no responseMay not be recordedNot applicable
UDPYes, with or without a replyThe application attempted to send, not that the traffic was delivered
ICMPNoNot applicable

Limitations of Event ID 3

Use these events to identify which processes communicate with IPv4 destinations. When reviewing the results, keep in mind that some activity may be missing and that the recorded fields provide limited information about the application’s behavior.

  • ICMP is not recorded. Event ID 3 covers TCP and UDP only, so ping to an IPv4 address leaves no event.
  • Failed TCP attempts can be missed. An application that repeatedly tries to reach an unresponsive IPv4 address may not appear in the log. This matters because unreachable destinations through WinCLAT time out rather than failing immediately.
  • Events show WinCLAT use, not literal use. An application that resolves a name to an IPv4 address and connects with an IPv4 socket produces the same event as an application that uses a literal IPv4 address. The destination is the resolved address in both cases, so Sysmon cannot confirm that an address is hard-coded. Sysmon Event ID 22 (DNS query) can provide supporting context, because it identifies the process that made a query, but the absence of a matching query is not proof of a literal. The configuration above does not log this event, so collecting it requires adding a DnsQuery rule.
  • Event counts are not traffic counts. Sysmon does not record one event per packet or per flow, so several UDP sends on one socket can produce a different number of events. Use the events to identify which applications communicate with which destinations, not to measure traffic volume.
  • Shared processes hide the service. Traffic from a Windows service can appear with an Image of svchost.exe. Use the ProcessId to identify the service while the process is still running.
  • Native IPv4 is excluded. On a computer with native IPv4 connectivity, some connections may use a native IPv4 source address instead of the WinCLAT source address. Those connections do not match this filter and are not included in the results.

Additional Troubleshooting Tools

If traffic that Sysmon does not record becomes important, such as ICMP or failed connection attempts, the following sources may help. Each has its own trade-offs, so evaluate them in your environment.

  • Windows Filtering Platform auditing. The Filtering Platform Connection audit subcategory records permitted and blocked connections in the Security event log as events 5156 and 5157, including the application where available. It can generate a high volume of events.
  • Packet capture. A capture on the physical adapter with a tool such as pktmon.exe can show translated IPv6 traffic, including ICMP and unanswered connection attempts. The IPv4 destination is embedded in the destination address under the NAT64 prefix. Packet headers alone do not identify the calling executable, so process attribution requires additional correlation.
  • NAT64 gateway logs. Depending on the gateway, its logs can show the client and destination of translated traffic, but not the application.

Summary

WinCLAT logs instance state changes but does not identify the applications using it. Sysmon Event ID 3, filtered on WinCLAT source addresses and with common local traffic excluded, provides a practical way to identify applications likely using WinCLAT. The events record the executable, user account, destination address, and port for matching TCP and UDP connections. They do not cover ICMP, may omit failed TCP attempts, and cannot distinguish a literal IPv4 address from an address obtained through name resolution. Use the results to identify applications for further investigation and confirm translation with a packet capture when needed.

Additional Information

Sysmon XML Configuration File for WinCLAT Tracing on GitHub

WinCLAT resources on directaccess.richardhicks.com

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

WEBINAR: Preparing for 100-Day Certificates with CertKit

Join me and the CertKit team on Tuesday, October 6, 2026, at 9:00 AM PDT for a free, live webinar about the upcoming reduction in public TLS certificate lifetimes. Beginning March 15, 2027, the maximum validity period for public TLS certificates will be reduced to 100 days. This change will make manual certificate management increasingly difficult for many organizations.

Automation

Shorter certificate lifetimes require organizations to identify, enroll, deploy, and renew certificates more frequently. Automation can help reduce the administrative effort and the risk of service interruptions caused by expired certificates. This is especially important for public-facing Microsoft workloads such as Internet Information Services (IIS), Remote Desktop Services (RDS), Always On VPN, DirectAccess, and other services that use public TLS certificates.

Visibility

Effective certificate management begins with knowing which certificates exist, where they are installed, and when they expire. Without this visibility, organizations may overlook certificates until they are close to expiration or have already expired.

Internal Certificates

Certificates issued by a private certification authority (CA) aren’t subject to the lifetime restrictions imposed on public TLS certificates. However, they still require inventory, monitoring, and renewal. A consistent approach to managing public and private certificates can help reduce operational overhead.

How CertKit Helps

CertKit is a cloud-based service for managing public and private TLS certificates. During the webinar, we’ll demonstrate how CertKit provides visibility into certificate inventories and expiration dates while automating common lifecycle tasks such as enrollment, deployment, and renewal. We’ll also review recent additions to the service.

Register Now

The webinar takes place on Tuesday, October 6, at 9:00 AM PDT. Registration is required. Everyone who registers will be notified when the session recording is available.

Live! 360 Event Orlando, Florida 2026

I’m excited to announce that I’ll be attending the upcoming Live! 360 Event, November 15-20, 2026, at Royal Pacific Resort at Universal Orlando, Florida. I’ll be in attendance all week and will be delivering a few talks at the event this year.

Sessions

I’ll be presenting two sessions at this year’s event. They are:

Join Me!

If you are planning to attend the event, please join my sessions! I will be at the conference center all week, so don’t hesitate to reach out and contact me while you are there. I’m looking forward to seeing everyone soon!

Always On VPN Security Updates September 2026

Microsoft released the September 2026 security updates today, which include numerous fixes affecting Always On VPN deployments. This month’s edition addresses vulnerabilities in Windows Server Routing and Remote Access (RRAS), VPN protocols such as Secure Socket Tunneling Protocol (SSTP) and Internet Key Exchange version 2 (IKEv2). The updates also include Active Directory Certificate Services (AD CS), a crucial supporting infrastructure service for Always On VPN.

RRAS

September 2026 Microsoft security updates include 8 CVEs for RRAS. Four are rated Critical, the most severe having a CVSS rating of 9.8.

RCEs

The following four CVEs are Remote Code Execution vulnerabilities. All are rated critical.

Privilege Escalation

The following two CVEs are RRAS privilege escalation vulnerabilities. All are rated Important.

Denial of Service

Finally, the last CVE addresses a denial-of-service vulnerability in RRAS.

VPN Protocols

The following section outlines vulnerabilities addressed in the September 2026 security updates affecting commonly used VPN protocols.

SSTP

The following four CVEs cover vulnerabilities in SSTP. One is rated critical with a CVSS score of 9.8. The rest are rated Important.

IKEv2

The following CVEs address vulnerabilities in the IKEv2 VPN protocol. All are rated important.

AD CS

Microsoft AD CS is commonly deployed to issue and manage certificates used for encryption and user and device authentication in Always On VPN deployments. The following four CVEs address vulnerabilities disclosed in AD CS. The first two are privilege escalation vulnerabilities, the third covers information disclosure, and the last addresses a tampering vulnerability. All are rated Important.

Summary

The September 2026 Microsoft security updates address several critical vulnerabilities affecting organizations that have deployed Microsoft Always On VPN. Administrators are encouraged to update their systems as soon as possible.

Additional Information

Microsoft September 2026 Security Updates

Intranet Certificate Monitoring with CertKit

CertKit is a cloud-based solution that automates the issuance and management of public TLS certificates. It also provides certificate monitoring and alerting for public-facing workloads. However, many organizations have internal (non-public-facing) services that also use TLS. CertKit agent v1.13.0, currently in preview, closes this gap by providing visibility into TLS certificates used by intranet resources. After installing the latest release of the agent, CertKit can now provide visibility into the status of TLS certificates for internal resources.

Intranet Monitoring

After installing or updating the CertKit agent to v1.13.0, administrators can select an internal TLS service to monitor. Follow the steps below to enable this feature.

Certificate Collection

I recommend creating a separate Certificate Collection to support intranet monitoring. In the CertKit management console, click Add Collection, enter a unique, descriptive name, and click Add Collection.

Install the Agent

Once the new collection is created, navigate to the Agents tab, select your platform, then download, install, and register the agent.

Monitor New Host

After the agent is installed and registered, navigate to the Monitoring tab and click Monitor New Host. Enter the fully qualified domain name (FQDN) of the resource and specify its TLS port. Under Host Visibility, select Internal, and then choose the agent to monitor the host from. When finished, click Monitor Host.

Note: The server running the CertKit agent does not require a TLS certificate of its own to monitor internal resources.

Monitored Hosts

CertKit can track certificates for any internal workload that uses TLS. In this example, the monitored resources include web applications, security appliances, load balancers, and HTTP CRL distribution points. The list also includes LDAPS on the domain controllers and the RDP and WinRM HTTPS services on the management workstation.

The circle next to each resource indicates its certificate status. Green indicates a healthy certificate, yellow indicates one approaching expiration, and red indicates an expired certificate or another detected issue.

Note: The RDP certificate on the management workstation appears red because it contains only the Remote Desktop Authentication EKU (1.3.6.1.4.1.311.54.1.2). It intentionally does not include Server Authentication, which CertKit currently expects when validating the service. CertKit is aware of this limitation and plans to address it in a future release.

Host Discovery

CertKit provides robust discovery for public websites but does not currently offer equivalent functionality for intranet resources. Administrators can identify internal systems listening on a specific port by using Nmap.

nmap.exe -Pn -p [port] --open [internal subnet]

For example:

nmap.exe -Pn -p 443 --open 172.16.0.0/24

Alternatively, add the -oX switch to save the output in XML format.

nmap.exe -Pn -p 443 --open 172.16.0.0/24 -oX scan.xml

The resulting Nmap XML file output can be converted to CSV format using this PowerShell code.

Summary

CertKit agent v1.13.0 extends certificate monitoring to internal TLS services, giving administrators greater visibility into certificates that were previously difficult to track. Although intranet host discovery remains a manual process, tools such as Nmap and PowerShell can help identify resources to add to the monitoring platform

Getting Started with CertKit

Need help improving certificate visibility and management across your organization? Want to automate public TLS certificate enrollment for workloads such as DirectAccess, Always On VPN, IIS, SQL, and more? I can help you assess your certificate environment, identify monitoring gaps, and develop a strategy for managing certificates across internal and public-facing workloads. Fill out the form below, and I’ll provide you with more information.

← Back

Thank you for your response. ✨

Additional Information

CertKit Website

What Is CertKit?

CerKit Agent Support for Always On VPN SSTP and DirectAccess IPHTTPS TLS Certificates

IIS TLS Certificate Deployment with CertKit

The Case for 6-Day Public TLS Certificates

DirectAccess IPHTTPS and Let’s Encrypt 6-Day TLS Certificates

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

Entra Internet Access TLS Inspection and Always On VPN: Troubleshooting SSTP Connection Failures

Microsoft Entra Global Secure Access (GSA) is a cloud-based Security Service Edge (SSE) solution that includes Entra Private Access to provide zero-trust network access to private data and applications, and Entra Internet Access to provide security controls for general internet access. Entra Internet Access includes features such as web content filtering, AI prompt controls, TLS inspection, and more. Entra Private Access and Entra Internet Access share a common client: the Global Secure Access Client.

TLS Inspection

TLS inspection is a powerful feature of Entra Internet Access that allows inspection and policy enforcement for encrypted internet traffic. It enables more thorough inspection and is required for features such as AI prompt policies. When TLS inspection is enabled, the TLS connection from the target server (origin server) is terminated by the Entra service. A new session is created between the cloud and the endpoint using a dynamically generated TLS certificate issued by Entra. As Entra holds the private key for this certificate, it can decrypt and inspect traffic as necessary.

Always On VPN

Recently, a customer asked me to help troubleshoot an Always On VPN user tunnel connectivity issue. The problem began shortly after deploying the Global Secure Access client with TLS inspection enabled. Administrators had configured the default TLS inspection policy to inspect traffic for all websites.

User Tunnel Failures

Attempts to manually start the Always On VPN user tunnel resulted in a failed connection attempt with the following error message.

Error 0x800704D4: The network connection was aborted by the local system.

Event Logs

Reviewing the client event logs revealed numerous Event ID 20227 entries from the RasClient source with the following error message.

The user DOMAIN\User dialed a connection named [connection name] which has failed. The error code returned on failure is -2147023660.

Note: Error code -2147023660 is the decimal equivalent of 0x800704D4.

Troubleshooting

Initial testing with Test-NetConnection confirmed that TCP port 443 on the VPN server was reachable. However, using Get-TlsCertificate revealed the real problem.

Although the certificate subject matched the VPN server, the issuer did not. Instead of the VPN server’s issuing CA, the certificate had been issued by Microsoft Entra Global Secure Access, confirming that TLS inspection was intercepting the connection.

SSTP and TLS Inspection

The Secure Socket Tunneling Protocol (SSTP) is a Microsoft proprietary VPN transport that uses HTTP for tunneling and TLS for security. Unlike a web browser, which can establish a new trusted TLS session with an inspection proxy, SSTP validates the VPN server’s certificate as part of establishing the VPN tunnel. Any certificate substitution, even by a trusted TLS inspection service, changes the server certificate thumbprint and causes SSTP validation to fail.

Workaround

The solution is to create a TLS inspection exclusion policy to exempt inspection for the VPN server FQDN(s), as shown here.

Summary

Microsoft Entra Internet Access TLS inspection can unintentionally interfere with Always On VPN deployments that use SSTP. Because TLS inspection replaces the VPN server’s certificate with one issued by Microsoft Entra, SSTP detects the certificate mismatch and terminates the connection. If you use Always On VPN with Entra Internet Access, configure a TLS inspection exclusion for your VPN server FQDNs to prevent interception while preserving TLS inspection for general internet traffic.

Additional Information

Always On VPN vs. Entra Private Access: Choosing the Right Access Model for your Organization

What is Microsoft Entra Global Secure Access?

Microsoft Entra Internet Access

Microsoft Entra Private Access

Always On VPN SSTP and 47-Day TLS Certificates

Always On VPN SSTP and HSTS