Always On VPN IKEv2 and SSTP Fallback

Always On VPN IKEv2 and SSTP FallbackA while back I wrote about the various VPN protocols supported for Windows 10 Always On VPN. The two most common are Internet Key Exchange version 2 (IKEv2) and Secure Socket Tunneling Protocol (SSTP). The article covers in detail each protocol’s advantages and disadvantages. To summarize, IKEv2 provides the best security (when configured correctly!) and SSTP is firewall-friendly ensuring ubiquitous access. Ideally an Always On VPN connection will attempt to use the more secure IKEv2 first, then fallback to SSTP only when IKEv2 is unavailable. Unfortunately, Always On VPN connections do not work this way today.

IKEv2 and SSTP

IKEv2 and SSTP are not mutually exclusive. When using Windows Routing and Remote Access Service (RRAS) as the VPN server, both protocols can be configured and enabled for VPN clients. To allow VPN clients to automatically select a protocol, the NativeProtocolType element in ProfileXML can be set to Automatic.

Always On VPN IKEv2 and SSTP Fallback

IKEv2 with SSTP Fallback?

In theory, with the NativeProtocolType set to Automatic, the Windows 10 client would first attempt to establish an IKEv2 connection, then fall back to SSTP if IKEv2 is not available. In practice, this is not the case.

SSTP Preferred over IKEv2

In operation, setting the NativeProtocolType to Automatic results in the Windows 10 client attempting to establish a VPN connection using SSTP first! If the SSTP connection fails, only then will IKEv2 be used. The only scenario in which I can imagine SSTP failing and IKEv2 being successful would be if SSTP is not supported by the VPN server. Sadly, this scenario may result in failed connections due to a bug in the way ProfileXML settings are processed. Details here.

VPN Strategy

The initial VPN protocol selection behavior is dictated by the VpnStrategy setting of the Always On VPN connection in the rasphone.pbk file. This file can be found under C:\Users\[username]\AppData\Roaming\Microsoft\Network\Connections\Pbk. The documentation on the Microsoft website is terribly outdated and does not include the following important VpnStrategy settings pertinent to Windows 10 Always On VPN connections.

  • 5 = Only SSTP is attempted
  • 6 = SSTP is attempted first
  • 7 = Only IKEv2 is attempted
  • 8 = IKEv2 is attempted first
  • 14 = IKEv2 is attempted followed by SSTP

Always On VPN Default Behavior

For Always On VPN, when the NativeProtocolType is set to Automatic in ProfileXML, VpnStrategy is set to 6 by default, which means the connection will attempt to use SSTP first. If it fails, IKEv2 will be attempted.

Always On VPN IKEv2 and SSTP Fallback

If the NativeProtocolType in ProfileXML is set to IKEv2, VpnStrategy is set to 7 and only IKEv2 is used. A connection using SSTP is never attempted.


Setting the VpnStrategy to 8 or 14 will force the client to attempt an IKEv2 connection first. However, this setting is dynamically updated by Windows and is subject to change. For example, if an IKEv2 connection fails and SSTP is successful, Windows will then set the VpnStrategy to 6 and all subsequent VPN connection attempts will use SSTP first. Because of this it will be necessary to update the VpnStrategy setting each time prior to establishing a VPN connection. This will require some clever scripting and perhaps automation using a scheduled task based on an event trigger. I will leave that custom configuration as an exercise for the reader. If you’ve developed something to address this challenge, please feel free to share in the comments below. 🙂

Additional Information

Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN IKEv2 Security Configuration

Always On VPN Certificate Requirements for IKEv2

Always On VPN IKEv2 Load Balancing with KEMP LoadMaster Load Balancer

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.


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

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