Entra Private Network Connector Session Persistence

The Microsoft Entra Private Network Connector is a lightweight on-premises software agent that enables Microsoft Entra Private Access to forward Global Secure Access (GSA) client traffic to internal resources. In environments with multiple connectors, traffic is normally distributed across available connectors in a connector group. While this improves resiliency and load distribution, it can create challenges for applications that rely on a consistent connector source IP address.

Stateless Connectors

By default, requests are distributed randomly among the available connectors in a connector group. Traffic forwarded to the internal resource uses the connector server’s IP address as its source. Consequently, separate connections from the same user and device can reach the application through different connectors. Importantly, session state is not shared among connectors in a connector group. As such, applications that associate session state with the source IP address may reject or interrupt these connections.

Why Session Persistence Matters

In some scenarios, an internal application might allow access only from specific connector IP addresses or associate an authenticated session with the source IP address. Random connector selection can cause subsequent connections to arrive from a different address, potentially interrupting the session. Session persistence reduces this risk by consistently using the same connector for the user and device.

Session Persistence

Microsoft recently introduced session persistence for Entra Private Access applications. When enabled, requests from the same user and device are consistently routed to the same connector for the duration of the session. This helps maintain a consistent connector egress IP address for applications that depend on source IP addresses for authentication, authorization, or session management.

Traffic Routing

The connector traffic routing method is configured on a per-application basis. Traffic routing methods can be defined on Quick Access or Enterprise applications, and the setting can be configured on the Network access properties tab. Administrators have two options: Random or Session Persistence.

Random

This is the default behavior for the Private Network connector. All new connections are distributed randomly among connectors in the connector group.

Session Persistence

Selecting the Session Persistence option consistently routes requests from the same user and device to the connector on which the session was established.

Connector Routing Method Comparison

The following table summarizes these configuration options.

Routing MethodBenefitsConsiderations
RandomBetter distribution across connectors in a connector groupSource IP address may change between connections
Session PersistenceConsistent connector egress IP addressMay not distribute sessions as evenly as the Random method

Failover

If the preferred connector becomes unavailable, subsequent traffic may be routed through another available connector. Applications that depend on the connector’s source IP address might require the user to establish a new session.

GSA Applications Only

Session persistence applies only to Global Secure Access applications. It is not supported for applications published using Microsoft Entra Application Proxy.

Summary

By default, Microsoft Entra Private Access distributes requests randomly among available connectors. Although this provides load distribution, it can create problems for applications that depend on a consistent connector source IP address. Session persistence addresses this issue by consistently routing traffic from the same user and device through the same connector for the duration of the session. This feature applies only to Global Secure Access applications and is not supported for Microsoft Entra Application Proxy applications.

Additional Information

Entra Private Network Connector Overview and Deployment Strategies

Preventing Port Exhaustion on Entra Private Network Connector Servers

Microsoft Entra Private Network Connector Groups

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

What’s New in Entra Private Network Connector v1.5.4892.0

An important update is available for the Microsoft Entra Private Network Connector. The Entra Private Network Connector is used to publish on-premises web applications to the internet. It is also used for Global Secure Access (GSA) with Entra Private Access, allowing GSA clients to access on-premises resources. Entra Private Network Connector v1.5.4892.0 includes important new functionality to streamline troubleshooting and improve stability and performance.

New Features

The Entra Private Network Connector v1.5.4892.0 now includes a diagnostic tool on the system tray. This gives administrators a visual indicator of connector status and provides quick access to diagnostics and log files.

Diagnostics

Right-clicking the connector and choosing ‘Connector diagnostics’ launches the Connector Diagnostics window. Here you’ll find three tabs: Overview, Health Check, and Advanced Logs.

Overview

The Overview tab provides details about the connector, such as the Tenant ID, Connector ID, version, supported TLS versions, the connector server’s IPv4 address (IPv6 information is not displayed), the server’s hostname, and the operating system version.

Health Check

Clicking on the Health Check tab will perform a comprehensive system health check. Status information for each check is provided, indicating whether it is Passed or Failed. Optionally, administrators can export the report in text, HTML, or JSON format for further analysis. Each health check can be expanded to reveal additional information about the individual check.

Advanced Logs

Clicking the Advanced Logs tab allows administrators to retrieve detailed log information. Session channel logging is enabled by default but can optionally be disabled if needed. You can choose specific start and end dates and times to collect logs, then click Retrieve Logs to collect them.

Once complete, it’s not immediately obvious where to find these logs. Clicking the Logs Retrieved button prompts the administrator to select a location in which to save the log files.

Improvements

This update improves the reliability of name resolution by filtering invalid DNS responses. In addition, the update improves connector logging to the Windows Event Log and fixes various issues and bugs.

Updating to v1.5.4892.0

Existing Entra Private Network Connector installations will not automatically receive this update. Administrators must manually download the connector from the Microsoft Entra admin center and apply the update themselves to take advantage of these new features and capabilities.

Additional Information

Microsoft Entra Private Network Connector v1.5.4892.0

Microsoft Entra Private Network Connector Overview and Deployment Strategies

Preventing Port Exhaustion on Entra Private Network Connector Servers