Always On VPN SSL Certificate Requirements for SSTP

Always On VPN Certificate Requirements for SSTPThe Windows Server 2016 Routing and Remote Access Service (RRAS) is commonly deployed as a VPN server for Windows 10 Always On VPN deployments. Using RRAS, Always On VPN administrators can take advantage of Microsoft’s proprietary Secure Socket Tunneling Protocol (SSTP) VPN protocol. SSTP is a Transport Layer Security (TLS) based VPN protocol that uses HTTPS over the standard TCP port 443 to encapsulate and encrypt communication between the Always On VPN client and the RRAS VPN server. SSTP is a firewall-friendly protocol that ensures ubiquitous remote network connectivity. Although IKEv2 is the protocol of choice when the highest level of security is required for VPN connections, SSTP can still provide very good security when implementation best practices are followed.

SSTP Certificate

Since SSTP uses HTTPS for transport, a common SSL certificate must be installed in the Local Computer/Personal/Certificates store on the RRAS VPN server. The certificate must include the Server Authentication Enhanced Key Usage (EKU) at a minimum. Often SSL certificates include both the Server Authentication and Client Authentication EKUs, but the Client Authentication EKU is not strictly required. The subject name on the certificate, or at least one of the Subject Alternative Name entries, must match the public hostname used by VPN clients to connect to the VPN server. Multi-SAN (sometimes referred to as UC certificates) and wildcard certificates are supported.

Always On VPN Certificate Requirements for SSTP

Certification Authority

It is recommended that the SSL certificate used for SSTP be issued by a public Certification Authority (CA). Public CAs typically have their Certificate Revocation Lists (CRLs) hosted on robust, highly available infrastructure. This reduces the chance of failed VPN connection attempts caused by the CRL being offline or unreachable.

Using an SSL certificate issued by an internal, private CA is supported if the CRL for the internal PKI is publicly available.

Key Type

RSA is the most common key type used for SSL certificates. However, Elliptic Curve Cryptography (ECC) keys offer better security and performance, so it is recommended that the SSTP SSL certificate be created using an ECC key instead.

Always On VPN Certificate Requirements for SSTP

To use an ECC key, be sure to specify the use of a Cryptographic Next Generation (CNG) key and select the ECDSA_P256 Microsoft Software Key Storage Provider (CSP) (or greater) when creating the Certificate Signing Request (CSR) for the SSTP SSL certificate.

Always On VPN Certificate Requirements for SSTP

Most public CAs will support certificate signing using ECC and Elliptic Curve Digital Signature Algorithm (ECDSA). If yours does not, find a better CA. 😉

Forward Secrecy

Forward secrecy (sometimes referred to as perfect forward secrecy, or PFS) ensures that session keys can’t be compromised even if the server’s private key is compromised. Using forward secrecy for SSTP is crucial to ensuring the highest levels of security for VPN connections.

To enforce the use of forward secrecy, the TLS configuration on the VPN server should be prioritized to prefer cipher suites with Elliptic Curve Diffie-Hellman Ephemeral (ECDHE) key exchange.

Authenticated Encryption

Authenticated encryption (AE) and authenticated encryption with associated data (AEAD) is a form of encryption that provides better data protection and integrity compared to older block or stream ciphers such as CBC or RC4.

To enforce the use of authenticated encryption, the TLS configuration on the VPN server should be prioritized to prefer cipher suites that support Galois/Counter Mode (GCM) block ciphers.

Important Note: In Windows Server 2016, GCM ciphers can be used with both RSA and ECC certificates. However, in Windows Server 2012 R2 GCM ciphers can only be used when an ECC certificate is used.

SSL Offload

Offloading SSL to a load balancer or application delivery controller (ADC) can be enabled to improve scalability and performance for SSTP VPN connections. I will cover SSL offload for SSTP in detail in a future post.

Summary

SSTP can provide good security for VPN connections when implementation and security best practices are followed. For optimum security, use an SSL certificate with an EC key and optimize the TLS configuration to use forward secrecy and authenticated cipher suites.

Additional Information

Always On VPN and Windows Server Routing and Remote Access Service (RRAS)

Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN Certificate Requirements for IKEv2

3 Important Advantages of Always On VPN over DirectAccess

Microsoft SSTP Specification on MSDN

Deploying Windows 10 Always On VPN with Microsoft Intune

Deploying Windows 10 Always On VPN with Microsoft IntuneWindows 10 Always On VPN is the replacement for Microsoft’s popular DirectAccess remote access solution. It provides the same seamless, transparent, always on remote connectivity as DirectAccess. Where DirectAccess relied heavily on classic on-premises infrastructure such as Active Directory and Group Policy, Always On VPN is infrastructure independent and is designed to be provisioned and managed using a Mobile Device Management (MDM) platform such as Microsoft Intune.

Intune and Always On VPN

Until recently, provisioning Windows 10 Always On VPN connections involved manually creating a ProfileXML and uploading to Intune using a custom profile. This has proven to be challenging for many, as the process is unintuitive and error prone.

A recent Intune update now allows administrators to create a basic Windows 10 Always On VPN deployment. Although it still has its limitations, it will go a long way to making the adoption of Always On VPN easier.

Prerequisites

Certificates must first be provisioned to all clients before deploying Windows 10 Always On VPN using Intune. In addition, if using a third-party VPN client, the VPN plug-in software must be installed prior to deploying the VPN profile.

Test VPN Connection

It is recommended that a test VPN connection be created on a client machine locally before deploying an Always On VPN profile using Intune. This allows the administrator to test connectivity and validate Extensible Authentication Protocol (EAP) settings. Once complete, run the following PowerShell commands to extract the EAP configuration settings to a file for later publishing with Intune.

$Vpn = Get-VpnConnection -Name [Test VPN connection name]
$Xml = $Vpn.EapConfigXmlStream.InnerXml | Out-File .\eapconfig.xml -Encoding ASCII

Deploying Always On VPN with Intune

Follow the steps below to deploy an Always On VPN connection using Intune.

Create a VPN Profile

  1. Open the Microsoft Intune management portal.
  2. Click Device configuration.
  3. Click Profiles.
  4. Click Create profile.

Deploying Windows 10 Always On VPN with Microsoft Intune

  1. Enter a name for the VPN profile.
  2. Enter a description (optional).
  3. From the Platform drop-down menu select Windows 10 and later.
  4. From the Profile type drop-down menu select VPN.
  5. In the Settings section click Configure.

Deploying Windows 10 Always On VPN with Microsoft Intune

Define VPN Profile Settings

  1. Click Base VPN.
  2. Enter a name for the connection.
  3. Enter a description and provide the Fully Qualified Domain Name (FQDN) of the VPN server. If it will be the default server select True and click Add.
  4. Enter a description and provide the FQDN for any additional VPN servers, as required.
  5. From the Connection type drop-down list choose the preferred connection type.
  6. In the Always On section click Enable.
  7. Select Enable to Remember credentials at each logon (optional).
  8. Click Select a certificate.
  9. Choose a client authentication certificate and click Ok.
  10. Paste the contents of eapconfig.xml (saved previously) in the EAP Xml field.
  11. Click Ok.

Deploying Windows 10 Always On VPN with Microsoft Intune

Define Additional Settings

You can also configure the following optional VPN settings using Intune.

  • Apps and Traffic Rules
  • Conditional Access
  • DNS Settings
  • Proxy
  • Split Tunneling

Deploying Windows 10 Always On VPN with Microsoft Intune

After configuring any required additional settings, click Create.

Assign VPN Profile

  1. Click Assignments.
  2. From the Assign to drop-down menu choose Selected Groups.
  3. Click Select groups to include.
  4. Choose an Azure Active Directory group to apply the VPN profile and click Select.
  5. Click Save.

Deploying Windows 10 Always On VPN with Microsoft Intune

Limitations

Although the ability to provision Always On VPN using Microsoft Intune without using a custom profile is welcome, it is not without its limitations. At the time of this writing, only Always On VPN user profiles can be configured. A device tunnel, which is optional, must be configured manually using a custom profile. In addition, the Intune user interface lacks the ability to define settings for the following parameters:

  • Exclusion routes
  • Name Resolution Policy Table (NRPT) exemptions
  • Lockdown mode
  • DNS registration
  • Trusted network detection
  • Custom IKEv2 cryptography policy

To make changes to the default settings for any of the above parameters, a ProfileXML must be created manually and provisioned with Intune using a custom policy.

Additional Information

Windows 10 Always On VPN Device Tunnel Step-by-Step Configuration using PowerShell

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN and the Name Resolution Policy Table (NRPT)

Windows 10 Always On VPN Hands-On Training

Always On VPN Certificate Requirements for IKEv2

Always On VPN Certificate Requirements for IKEv2Internet Key Exchange version 2 (IKEv2) is one of the VPN protocols supported for Windows 10 Always On VPN deployments. When the VPN server is Windows Server 2016 with the Routing and Remote Access Service (RRAS) role configured, a computer certificate must first be installed on the server to support IKEv2. There are some unique requirements for this certificate, specifically regarding the subject name and Enhanced Key Usage (EKU) configuration. In addition, some deployment scenarios may require a certificate to be provisioned to the client to support IKEv2 VPN connections.

Server Certificate

The IKEv2 certificate on the VPN server must be issued by the organization’s internal private certification authority (CA). It must be installed in the Local Computer/Personal certificate store on the VPN server. The subject name on the certificate must match the public hostname used by VPN clients to connect to the server, not the server’s hostname. For example, if the VPN server’s hostname is VPN1 and the public FQDN is vpn.example.net, the subject field of the certificate must include vpn.example.net, as shown here.

Always On VPN Certificate Requirements for IKEv2

In addition, the certificate must include the Server Authentication EKU (1.3.6.1.5.5.7.3.1). Optionally, but recommended, the certificate should also include the IP security IKE intermediate EKU (1.3.6.1.5.5.8.2.2).

Always On VPN Certificate Requirements for IKEv2

Client Certificate

Client certificate requirements vary depending on the type of VPN tunnel and authentication method being used.

User Tunnel

No certificates are required on the client to support IKEv2 when using MSCHAPv2, EAP-MSCHAPv2, or Protected EAP (PEAP) with MSCHAPv2. However, if the option to verify the server’s identity by validating the certificate is selected when using PEAP, the client must have the certificates for the root CA and any subordinate CAs installed in its Trusted Root Certification and Intermediate Certificate Authorities certificate stores, respectively.

User Tunnel with Certificate Authentication

Using certificate authentication for the user tunnel is the recommended best practice for Always On VPN deployments. A client certificate must be installed in the Current User/Personal store to support PEAP authentication with smart card or certificate authentication. The certificate must include the Client Authentication EKU (1.3.6.1.5.5.7.3.2).

Always On VPN Certificate Requirements for IKEv2

Device Tunnel

A computer certificate must be installed in the Local Computer/Personal certificate store to support IKEv2 machine certificate authentication and the Always On VPN device tunnel. The certificate must include the Client Authentication EKU (1.3.6.1.5.5.7.3.2).

Always On VPN Certificate Requirements for IKEv2

More information about configuring the Always On VPN device tunnel can be found here.

Additional Information

Always On VPN with Trusted Platform Module (TPM) Certificates

Always On VPN Protocol Recommendations for Windows Server 2016 RRAS

Always On VPN and Windows Server RRAS

Always On VPN Training

DirectAccess IP-HTTPS and Symantec SSL Certificates

DirectAccess IP-HTTPS and Symantec SSL CertificatesAn SSL certificate is required to support the IP-HTTPS IPv6 transition technology when configuring DirectAccess. Implementation best practices dictate using a public SSL certificate signed by a trusted third-party vendor such as Entrust, Verisign, DigiCert, and others. SSL certificates issued by a private PKI are acceptable if the client trusts the issuing CA. Self-signed certificates are supported in some deployment scenarios, but their use is generally discouraged. For more detailed information regarding SSL certificate considerations for DirectAccess IP-HTTPS click here.

Symantec Issued Certificates

Symantec is a popular commercial SSL certificate provider that has been commonly used for many years. However, due to integrity issues associated with their PKI management practices, Google and Mozilla announced they will soon be deprecating these certificates. This means users who browse to an HTTPS web site protected with a Symantec SSL certificate will receive a warning in their browser indicating the certificate is not trusted.

DirectAccess IP-HTTPS

It is important to note that there is no impact at all for DirectAccess when the server is configured to use an SSL certificate issued by Symantec. There is nothing you need to do to address this issue in this scenario. However, if a wildcard certificate is installed on the DirectAccess server and it is also used on other public-facing web servers in the organization, it is likely that the certificate will replaced, perhaps by another certificate provider. In this case, DirectAccess IP-HTTPS must be configured to use the new or updated SSL certificate.

Updating IP-HTTPS SSL Certificate

To update the DirectAccess IP-HTTPS SSL certificate, import the SSL certificate along with the private key in to the local computer certificate store on each DirectAccess server. Next identify the thumbprint of the new SSL certificate. Finally, open an elevated PowerShell command window and enter the following command.

$thumbprint = “ssl_cert_thumbprint”
$cert = Get-ChildItem -Path cert:\localmachine\my | where {$_.thumbprint -eq $thumbprint}
Set-RemoteAccess -SslCertificate $cert -PassThru

Be sure to replace “ssl_cert_thumbprint” with the actual thumbprint of your SSL certificate. 😉 In addition, for load-balanced and/or multisite deployments, run these PowerShell commands on each server in the enterprise.

Additional Information

SSL Certificate Considerations for DirectAccess IP-HTTPS

DirectAccess IP-HTTPS Null Cipher Suites Not Available 

DirectAccess IP-HTTPS Performance Issues

Troubleshooting Always On VPN Errors 691 and 812

Troubleshooting Always On VPN Errors 691 and 812When configuring Windows 10 Always On VPN using the Routing and Remote Access Service (RRAS) on Windows Server 2012 R2 and Extensible Authentication Protocol (EAP) authentication using client certificates, clients attempting to establish a VPN connection using Internet Key Exchange version 2 (IKEv2) may receive the following error.

“The connection was prevented because of a policy configured on your RAS/VPN server. Specifically, the authentication method used by the server to verify your username and password may not match the authentication method configured in your connection profile.”

Troubleshooting Always On VPN Errors 691 and 812

The event log on the client also records RasClient event ID 20227 stating “the error code returned on failure is 812”.

Troubleshooting Always On VPN Errors 691 and 812

Always On VPN clients using the Secure Socket Tunneling Protocol (SSTP) may receive the following error.

“The remote connection was denied because the user name and password combination you provided is not recognized, or the selected authentication protocol is not permitted on the remote access server.”

Troubleshooting Always On VPN Errors 691 and 812

The event log on the client also records RasClient event ID 20227 stating “the error code returned on failure is 691”.

Troubleshooting Always On VPN Errors 691 and 812

Resolution

These errors can occur when Transport Layer Security (TLS) 1.0 has been disabled on the RRAS server. To restore functionality, enable TLS 1.0 protocol support on the RRAS server. If disabling TLS 1.0 is required for compliance reasons, consider deploying RRAS on Windows Server 2016. TLS 1.0 can be safely disabled on Windows Server 2016 without breaking EAP client certificate authentication for Windows 10 Always On VPN clients.

Additional Information

Windows 10 Always On VPN Hands-On Training

What’s the Difference Between DirectAccess and Windows 10 Always On VPN?

5 Important Things DirectAccess Administrators Should Know About Windows 10 Always On VPN

3 Important Advantages of Windows 10 Always On VPN over DirectAccess 

Windows 10 Always On VPN and the Future of DirectAccess

DirectAccess and Always On VPN with Trusted Platform Module (TPM) Certificates

DirectAccess and Always On VPN with Trusted Platform Module (TPM) CertificatesTo enhance security when provisioning certificates for DirectAccess (computer) or Windows 10 Always On VPN (user) it is recommended that private keys be stored on a Trusted Platform Module (TPM) on the client device. A TPM is a dedicated security processor included in nearly all modern computers. It provides essential hardware protection to ensure the highest levels of integrity for digital certificates and is used to generate, store, and restrict the use of cryptographic keys. It also includes advanced security and protection features such as key isolation, non-exportability, and anti-hammering to prevent brute-force attacks.

To ensure that private keys are created and stored on a TPM, the certificate template must be configured to use the Microsoft Platform Crypto Provider. Follow the steps below to configure a certificate template required to use a TPM.

  1. Open the Certificate Templates management console (certtmpl.msc) and duplicate an existing certificate template. For example, if creating a certificate for DirectAccess, duplicate the Workstation Authentication certificate template. For Always On VPN, duplicate the User certificate template.
  2. On the Compatibility tab, ensure the Certification Authority and Certificate recipient compatibility settings are set to a minimum of Windows Server 2008 and Windows Vista/Server 2008, respectively.DirectAccess and Always On VPN with Trusted Platform Module (TPM) Certificates
  3. Select the Cryptography tab.
  4. Choose Key Storage Provider from the Provider Category drop down list.
  5. Choose the option Requests must use one of the following providers and select Microsoft Platform Crypto Provider.DirectAccess and Always On VPN with Trusted Platform Module (TPM) Certificates

Note: If Microsoft Platform Crypto Provider does not appear in the list above, got to the Request Handling tab and uncheck the option Allow private key to be exported.

Complete the remaining certificate configuration tasks (template display name, subject name, security settings, etc.) and publish the certificate template. Client machines configured to use this template will now have a certificate with private key fully protected by the TPM.

Additional Resources

Trusted Platform Module (TPM) Fundamentals

DirectAccess and Always On VPN Certificate Auto Enrollment

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