Managed Certificates for Remote Desktop Protocol

The Remote Desktop Protocol (RDP) is arguably the most widely used protocol for Windows remote server administration. RDP uses Transport Layer Security (TLS) for server authentication, data encryption, and integrity. However, the default configuration of TLS for RDP in Windows is less than ideal.

RDP Self-Signed Certificate

By default, RDP uses a self-signed certificate for TLS operations. TLS with self-signed certificates is a bad security practice because they are not validated by a trusted certificate authority (CA), making it impossible for clients to verify the authenticity of the server they are connecting to, which can lead to interception attacks.

Certificate Warning

Most administrators have encountered a warning error when connecting to a remote host via RDP using a self-signed RDP certificate.

“The remote computer could not be authenticated due to problems with its security certificate. It may be unsafe to proceed.”

Nmap

You can view the default self-signed certificate with the Nmap utility by running the following command.

nmap.exe -n -p 3389 <hostname> –script ssl-cert

Managed Certificates

A better solution for RDP TLS is to use managed certificates issued by an enterprise Public Key Infrastructure (PKI) such as Microsoft Active Directory Certificate Services (AD CS). AD CS is widely deployed in AD domain environments and can be configured to issue certificates for RDP TLS.

AD CS

To configure AD CS to issue RDP certificates, perform the following steps.

Certificate Template

On an issuing CA or an administrative workstation with the Remote Server Administration Tools (RSAT) installed, open the Certificate Templates management console (certtmpl.msc) and perform the following steps.

*My apologies for the list numbering format issues below. Microsoft Word and WordPress can’t seem to agree on the list format. Hopefully, you can figure it out, though. 🙂

  1. Right-click the Workstation Authentication template and choose Duplicate Template.
  2. Select the Compatibility tab.
    1. Select the operating system (OS) version corresponding to the oldest OS hosting the issuing CA role in your environment from the Certification Authority drop-down list.
    1. Select the OS version corresponding to your environment’s oldest supported server or client OS from the Certificate recipient drop-down list.
  3. Select the General tab.
    1. Enter a descriptive name in the Template display name field.
    1. Select an appropriate validity period for your environment. The best practice is to limit the validity period to one year or less.
  4. Select the Cryptography tab.
    1. From the Provider Category drop-down list, choose Key Storage Provider.
    1. From the Algorithm name drop-down list, choose RSA.
    1. In the Minimum key size field, enter 2048.
    1. From the Request hash drop-down list, choose SHA256.
  5. Select the Subject Name tab.
    1. From the Subject name format drop-down list, select DNS name.
    1. Ensure that DNS name is also checked in the subject alternate name section.
  6. Select the Extensions tab.
    1. Click on Application Policies.
    1. Click Edit.
    1. Select Client Authentication.
    1. Click Remove.
    1. Click Add.
    1. Click New.
    1. Enter Remote Desktop Authentication in the Name field.
    1. Enter 1.3.6.1.4.1.311.54.1.2 in the Object identifier field.
    1. Click Ok.
    1. Select Remote Desktop Authentication.
    1. Click Ok.
  7. Select the Security tab.
    1. Click Domain Computers.
    1. Grant the Read and Enroll permissions.
  8. Click Ok.

Next, open the Certification Authority management console (certsrv.msc) and follow the steps below to publish the certificate.

  1. Expand the CA.
  2. Right-click Certificate Templates and choose New > Certificate Template to Issue.
  3. Select the Remote Desktop Authentication certificate template.
  4. Click Ok.

Group Policy

Next, on a domain controller or a workstation with the RSAT tools installed, open the Group Policy Management console (gmpc.msc) and perform the following steps to create a new GPO to enroll domain computers for the Remote Desktop Authentication certificate

  1. Right-click Group Policy Objects and choose New.
  2. Enter a descriptive name for the GPO in the Name field.
  3. Click Ok.
  4. Right-click the GPO and choose Edit.
  5. Navigate to Computer Configuration > Policies > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Security.
  6. Double-click Server authentication certificate template.
  7. Select Enabled.
  8. Enter the name of the Remote Desktop Authentication certificate template in the Certificate Template Name field. Note: Be sure to enter the template name, not the template display name!
  9. Click Ok.

Once complete, link the GPO to the domain or OU to target the servers and workstations to which you wish to deploy the RDP certificate.

Validate Certificate

After updating group policy on a target resource, you’ll find that Nmap now shows the enterprise PKI-issued certificate used for RDP connections.

Additional Information

Understanding the Remote Desktop Protocol (RDP)

Always On VPN and SQL Target Principal Name Incorrect

Microsoft Always On VPN provides seamless and transparent remote access to corporate applications and data. In most cases, accessing resources over the VPN works the same as on-premises. However, a few folks have asked recently about an issue they found when using the SQL Server Management Studio (SMSS) to connect to a remote SQL server over Always On VPN.

Principal Name Incorrect

Administrators may encounter the following error message when using SMSS to connect to Microsoft SQL servers over an Always On VPN connection.

“The target principal name is incorrect. Cannot generate SSPI context. (Microsoft SQL Server)”

Resolution

There are a few different ways to resolve this issue. Choose the option that works best in your environment.

VPN Configuration

For Always On VPN deployments with Windows 11 24H2 and later clients, add the following setting to your XML configuration file.

<UseRasCredentials>false</UseRasCredentials>

For clients older than Windows 11 24H2, you must edit the rasphone.pbk file setting as follows.

UseRasCredentials=0

Group Policy

Optionally, a Group Policy Object (GPO) can be created and applied to target endpoints. For testing, you can enable this setting using the local group policy editor (gpedit.msc). Using either method, enable the following group policy setting.

Computer Configuration > Windows Settings > Security Settings > Local Policies > Security Options > Network access: Do not allow storage of passwords and credentials for network authentication = Enabled

Registry Editor

This method can be used for local testing. Open the Windows Registry Editor (regedit.exe) on a test client and create the following entry.

Key = HKLM\SYSTEM\CurrentControlSet\Control\Lsa
Name = DisableDomainCreds
Type = DWORD
Value = 1

PowerShell

The following PowerShell command will also create the required registry entry. Administrators can run the command interactively or deploy it via automation.

Set-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\Lsa’ -Name DisableDomainCreds -Value 1

Additional Information

Always On VPN Short Name Access Failure

Always On VPN Intermittent 13801 Error

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

Client Authentication

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

Certificate Selection

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

Resolution

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

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

Certificate Template

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

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

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

Force Renewal

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

On-Premises

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

Intune

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

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

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

PowerShell

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

Root CA

Open a PowerShell command window and run the following command.

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

Application Policy

Open a PowerShell command window and run the following command.

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

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

Intune Remediation

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

Summary

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

Additional Information

Troubleshooting Always On VPN Error 13801

Troubleshooting Always On VPN Error 13806

Troubleshooting Always On VPN Error 13868