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 ECDSA SSL Certificate Request for SSTP

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

Enabling Secure Remote Administration for the NetMotion Mobility Console

During the initial setup of a NetMotion Mobility gateway server, the administrator must choose to allow either Secure (HTTPS) or Non-secure (HTTP) connections when using the web-based Mobility Console.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Configuring HTTPS

Security best practices dictate HTTPS should be enabled to protect credentials used to log on to the gateway remotely. Immediately after selecting the Secure (https:) option, the administrator is prompted to enter server certificate information. Enter this information and click OK to continue and complete the rest of the configuration as necessary.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Self-Signed Certificate

When logging in to the Mobility console, the administrator is presented with a certificate error indicating there is a problem with the website’s security certificate. This is because the certificate is self-signed by the NetMotion Mobility gateway server and is not trusted.

Enabling Secure Remote Administration for the NetMotion Mobility Console

PKI Issued Certificate

The recommended way to resolve this is to request a certificate from a trusted certification authority (CA). To do this, open the Mobility Management Tool on the Mobility gateway server and click on the Web Server tab.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click on the Server Certificate button and then click New in the Certificate Request section.

Enabling Secure Remote Administration for the NetMotion Mobility Console

In the SAN (subject alternative name) field of the Optional Extension section enter the Fully Qualified Domain Name (FQDN) of the server using the syntax dns:fqdn. Include both the FQDN and the single-label hostname (short name) separated by a comma to ensure both names work without issue. For example:

dns:nm1.lab.richardhicks.net,dns:nm1

Enabling Secure Remote Administration for the NetMotion Mobility Console

Before requesting a certificate from a CA, the root and any intermediate CA certificates must first be imported. Click the Import button next to each, as required.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click Copy in the Certificate Request section to copy the Certificate Signing Request (CSR) to the clipboard and then save it to a text file. Now submit the CSR to be signed by the CA using the certreq.exe command. Open an elevated command or PowerShell window and enter the following commands.

certreq.exe -attrib “CertificateTemplate:[TemplateName]” -submit [Path_to_CSR_file]

For example:

certreq.exe -attrib “CertificateTemplate:LabWebServer” -submit certreq.txt

Select a CA from the list and click OK, then save the certificate response when prompted.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click Response and specify the location of the certificate response file saved in the previous step.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Once complete, the newly issued certificate will be in place. Click Close to complete the process.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Click Yes when prompted to restart the Mobility console.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Trusted Certificate

Opening the Mobility Console no longer produces a certificate error message with a certificate installed from a trusted CA.

Enabling Secure Remote Administration for the NetMotion Mobility Console

In addition, if you followed the guidance above and included the single-label hostname in the SAN field, accessing the server using the short name will also work without issue.

Enabling Secure Remote Administration for the NetMotion Mobility Console

Summary

Always select the option to use HTTPS to ensure the highest level of security and protection of credentials when remotely administering a NetMotion Mobility gateway server. For optimal security and to provide the best user experience, use a certificate issued and managed by a trusted CA to prevent certificate errors when opening the Mobility console.

Additional Information

NetMotion Mobility as an Alternative to DirectAccess

NetMotion Mobility Device Tunnel Configuration

Comparing NetMotion Mobility and DirectAccess Part 1 – Security

Comparing NetMotion Mobility and DirectAccess Part 2 – Performance

DirectAccess and NetMotion Mobility Webinar

 

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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