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 Security Updates August 2024

Today is the second Tuesday of the month, so Windows Server administrators everywhere know what that means – it’s Update Tuesday! For Always On VPN administrators in particular there are a few security updates that affect Windows Server Routing and Remote Access (RRAS), which is a popular VPN server used to support Always On VPN implementations. While many of these updates address Remote Code Execution vulnerabilities, non are considered critical.

RRAS Updates

This month there are six vulnerabilities disclosed affecting Windows Server RRAS.

CVE-2024-38120 – Windows RRAS Remote Code Execution Vulnerability (Important)

CVE-2024-38121 – Windows RRAS Remote Code Execution Vulnerability (Important)

CVE-2024-38128 – Windows RRAS Remote Code Execution Vulnerability (Important)

CVE-2024-38130 – Windows RRAS Remote Code Execution Vulnerability (Important)

CVE-2024-38154 – Windows RRAS Remote Code Execution Vulnerability (Important)

CVE-2024-38214 – Windows RRAS Remote Code Execution Vulnerability (Important)

Additional Updates

In addition to the updates addressing vulnerabilities in Windows Server RRAS, there are also updates available for the Windows Network Address Translation (NAT), Windows Transport Layer Security (TLS), and Windows IP Routing Management snapin that could potentially impact Always On VPN deployments.

Recommendations

None of the security vulnerabilities disclosed this month are critical. Although the RRAS vulnerabilities are remote code execution, exploitation is unlikely. However, administrators are encouraged to update their systems as soon as possible.

Additional Information

Microsoft August 2024 Security Updates

Always On VPN and Blast-RADIUS

Microsoft released an update for the Windows Server Network Policy Server (NPS) to address recently disclosed vulnerabilities in the Remote Access Dial-In User Service (RADIUS) protocol in the July 2024 security updates. RADIUS is an industry-standard authentication protocol widely used for remote access, including Always On VPN. The RADIUS protocol was first introduced in the early 1990s and, unfortunately, still relies on the deprecated MD5 cryptographic hash function. The good news is that this vulnerability does not affect Always On VPN. Read on to learn more.

Blast-RADIUS

Blast-RADIUS is an attack on the RADIUS protocol that allows an attacker to alter network authentication packets to gain access to a service relying on RADIUS for authentication by exploiting the weakness of MD5 integrity checks in RADIUS. In the absence other controls, an attacker could alter an authentication response and change the reply from Access-Reject to Access-Accept.

Considerations

It’s important to note that leveraging this attack is not trivial. It requires local network access, so the attacker must have a presence on the target network to carry out this attack. However, cloud-hosted RADIUS services are inherently more vulnerable. In addition, the attack is mostly academic today because the default timeout for authentication requests is typically short, usually between 5 and 30 seconds. This is not enough time (today) for an attacker to mount the attack. However, this attack could become more feasible if authentication timeouts are increased (sometimes required to support MFA) or if an attacker has access to vast computing resources.

Affected Protocols

Although Blast-RADIUS is a vulnerability in the RADIUS protocol itself, not all authentication protocols are affected. Specifically, this vulnerability affects services leveraging PAP, CHAP, MS-CHAP, and MS-CHAPv2. Extensible Authentication Protocol (EAP) and Protected Extensible Authentication Protocol (PEAP) are not vulnerable to this attack. Since Always On VPN requires EAP authentication, it is not susceptible to this attack.

Mitigation

Microsoft has published guidance in KB5040268 for mitigating Blast-RADIUS attacks on Windows NPS servers. Specifically, administrators are encouraged to enable the Message-Authenticator attribute in Access-Request packets sent by the network access server and to ensure the NPS server requires the Message-Authenticator attribute in any Access-Request messages it receives.

Note: The following changes are not required for Always On VPN or any other workload using EAP-TLS or Protected EAP, as these protocols use TLS natively to protect the authentication exchange.

NPS

To configure this setting in the UI, open the NPS management console (nps.msc) and perform the following steps.

  1. Expand RADIUS Clients and Servers.
  2. Highlight RADIUS Clients.
  3. Right-click the RADIUS client to configure and choose Properties.
  4. Select the Advanced tab.
  5. Check the box next to Access-Request messages must contain the Message-Authenticator attribute.

PowerShell

To configure this setting using PowerShell, open an elevated PowerShell command window and run the following command.

Set-NpsRadiusClient -Name <RADIUS client name> -AuthAttributeRequired $True

Additional NPS Settings

Administrators should also run the following commands on their NPS servers to further protect their infrastructure from Blast-RADIUS attacks.

netsh.exe nps set limitproxystate all = enable

netsh.exe nps set requiremsgauth all = enable

RRAS

When using Windows Server Routing and Remote Access (RRAS) without EAP, ensure the RADIUS server configuration always includes the Message-Authenticator. To configure this setting, open the Routing and Remote Access console (rrasmgmt.msc) on the RRAS server and perform the following steps.

  1. Right-click the VPN server and choose Properties.
  2. Select the Security tab.
  3. Click the Configure button next to the Authentication provider drop-down list.
  4. Highlight the RADIUS server and choose Edit.
  5. Check the box next to Always use message authenticator.

Repeat these steps for any additional configured RADIUS servers.

CLI

Administrators can implement this change at the command line by opening an elevated command window and entering the following command.

netsh.exe ras aaaa set authserver name = <name of RADIUS server> signature = enabled

For example:

netsh.exe ras aaaa set authserver name = nps.lab.richardhicks.net signature = enabled

New NPS Events

After installing the KB5040268 update on NPS servers, the NPS server will record event ID 4421 from the NPS source after a service start if the RequireMsgAuth or LimitProxyState settings are not configured.

“RequireMsgAuth and/or limitProxyState configuration is in Disable mode. These settings should be configured in Enable mode for security purposes.”

Optional Mitigation

If administrators cannot configure the above settings, consider using IPsec to secure network traffic at the transport layer. IPsec will protect all RADIUS traffic at the network layer to mitigate Blast-RADIUS attacks. Unfortunately, Windows Server NPS does not support TLS or DTLS, so IPsec is your only option.

Summary

Always On VPN is not vulnerable to the Blast-RADIUS attack. However, NPS is commonly a shared service in many organizations, and other workloads may use older, vulnerable protocols. Consider implementing the changes detailed in KB5040268 as outlined in above to ensure the integrity of your environment and mitigate these potential attacks.

More Information

Microsoft KB5040268: how to manage Access-Request packets attack vulnerability associated with CVE-2024-3596

RADIUS Protocol Vulnerability Exposes Networks to MitM Attacks

New Blast-RADIUS attack breaks 30-year-old protocol used in networks everywhere

Overview of Microsoft Protected Extensible Authentication Protocol (PEAP)

Always On VPN NPS Auditing and Logging