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

DirectAccess IP-HTTPS Null Cipher Suites Not Available

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableMicrosoft first introduced support for null cipher suites for the IP-HTTPS IPv6 transition technology in Windows Server 2012, and it is supported for DirectAccess in Windows 8.x and Windows 10 clients. Using null cipher suites for IP-HTTPS eliminates the needless double encryption that occurs when using encrypted cipher suites. DirectAccess is a unique workload where SSL/TLS encryption isn’t really required because the payload being transported in HTTPS is already encrypted.

No Encryption by Design

When supporting Windows 8.x and Windows 10 clients, ensuring null cipher suites (TLS_RSA_WITH_NULL_SHA and TLS_RSA_WITH_NULL_SHA256) are enabled and operational is crucial to providing the highest levels of performance and scalability for the remote access solution. When following implementation best practices, this isn’t really an issue. However, in some cases null cipher suites may be disabled. This will result in reduced scalability and degraded performance for Windows 8.x and Windows 10 clients.

Validating SSL/TLS Configuration

The easiest way to verify that null cipher suites are being offered by the DirectAccess server is to use the Qualys SSL Labs server test site. Ideally you should see a result similar to this.

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableFigure 1. Qualys SSL Labs server test site results for properly configured DirectAccess server.

Don’t be alarmed by the overall rating “F”. That happens because the Qualys test site is designed to test web servers where using null cipher suites would be a serious security issue. As I stated previously, the DirectAccess workload is unique in that its HTTPS payload is already encrypted, so using null cipher suites is acceptable in this scenario.

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableFigure 2. Qualys SSL Labs server test site results for properly configured DirectAccess server showing support for null SSL/TLS cipher suites.

Null Cipher Suites Missing

When performing the Qualys SSL labs server test on a DirectAccess server, an overall rating of “A” is not desirable and indicates the DirectAccess server is misconfigured. This is caused by the lack of support for null cipher suites.

DirectAccess IP-HTTPS Null Cipher Suites Not AvailableFigure 3. Qualys SSL Labs server test site results for misconfigured DirectAccess server.

Common Causes

Null cipher suites for SSL and TLS can be disabled for a variety of reasons. Below are some of the most common causes for the lack of support for null cipher suites for DirectAccess.

Self-Signed Certificates – Using the Getting Started Wizard (simplified deployment) will configure DirectAccess using a self-signed certificate for IP-HTTPS. Using a self-signed certificate is discouraged for numerous reasons, most importantly because it disables support for null cipher suites.

Security Hardening – Security administrators may proactively disable support for null cipher suites in a misguided effort to “improve security” for DirectAccess. While this is acceptable and recommended on a web server, it is not advisable to disable null cipher suites on a DirectAccess server.

SSL Certificate Signing Algorithm – Using an SSL certificate signed with an Elliptical Curve (EC) key as opposed to an RSA key will result in the loss of support for null cipher suites for IP-HTTPS. High security/assurance certificates signed with EC keys are not recommended for use on DirectAccess servers and should be avoided if possible.

DirectAccess Configuration Options – Enabling One-Time Password (OTP) authentication on the DirectAccess server will also result in a loss of support for null cipher suites. Also, adding additional roles to the DirectAccess server such as client-based VPN or the Web Application Proxy (WAP) can also result in null cipher suites being disabled.

Summary

Null cipher suites are implemented by design on DirectAccess servers to enhance performance for Windows 8.x and Windows 10 clients and improve overall scalability for the implementation. They eliminate the pointless double encryption of DirectAccess communication, which itself is already encrypted. For optimal performance and scalability, be sure to follow implementation best practices and use a PKI-managed (public or private) SSL certificate signed with an RSA key (SHA-256 recommended). Resist the urge to “harden” the DirectAccess server by disabling support for null cipher suites, and avoid the use of SSL certificates signed with EC keys. In addition, carefully consider DirectAccess deployment options such as OTP authentication and consider deploying roles such as VPN and WAP on a separate server.

Additional Information

DirectAccess IP-HTTPS SSL and TLS Insecure Cipher Suites

DirectAccess IP-HTTPS Null Encryption and SSTP VPN

DirectAccess and FIPS Compliant Algorithms for Encryption

SSL Certificate Considerations for DirectAccess IP-HTTPS 

 

 

SSL Certificate Considerations for DirectAccess IP-HTTPS

SSL Certificate Considerations for DirectAccess IP-HTTPSDirectAccess uses IPv6 exclusively for communication between the client and server. IPv6 transition technologies are used to support DirectAccess communication over the IPv4 public Internet. One of those IPv6 transition technologies, IP-HTTPS, uses HTTP for encapsulation and SSL/TLS for authentication of the DirectAccess server.

SSL Certificates

When configuring DirectAccess, an SSL certificate must be provided for IP-HTTPS. There are three different types of SSL certificates that can be used.

Public SSL Certificate – Using an SSL certificate signed by a public certification authority (CA) is the recommended best practice for configuring DirectAccess IP-HTTPS. This provides the highest level of assurance for DirectAccess clients connecting via IP-HTTPS.

Private SSL Certificate – Using an SSL certificate issued by the organization’s internal CA is an acceptable alternative to using a public SSL certificate in most cases. This can reduce the cost associated with obtaining the certificate, especially for multisite deployments.

Self-Signed Certificate – Using a self-signed certificate is not recommended and should be avoided in most deployment scenarios. A self-signed certificate provides no real assurance for DirectAccess clients. Crucially, using a self-signed certificate will disable support for null SSL and TLS cipher suites. This reduces the overall scalability and performance of the remote access solution.

SSL Certificate Considerations for DirectAccess IP-HTTPS

Figure 1. Null cipher suites not supported when using a self-signed SSL certificate for IP-HTTPS.

Certificate Requirements

The SSL certificate must include the Server Authentication (1.3.6.1.5.5.7.3.1) Enhanced Key Usage (EKU) Object Identifier (OID). It should use an RSA key of 2048 bits and be signed with SHA256. Using stronger keys provides no additional protection and should not be used. In addition, SSL certificates using ECDSA keys is not recommended, as they do not support null cipher suites.

Summary

In most cases, using a public SSL certificate is ideal. However, issuing a certificate from a private CA is also acceptable. Using self-signed certificates can be used for non-production testing and in very small production deployments, but should generally be avoided.

Additional Resources

DirectAccess IP-HTTPS SSL and TLS Insecure Cipher Suites

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

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