Always On VPN SSTP Security Configuration

Always On VPN SSTP Security Configuration

When using Windows Server Routing and Remote Access Service (RRAS) to terminate Always On VPN client connections, administrators can leverage the Secure Socket Tunneling Protocol (SSTP) VPN protocol for client-based VPN connections. SSTP is a Microsoft proprietary VPN protocol that uses Transport Layer Security (TLS) to secure connections between the client and the VPN gateway. SSTP provides some crucial advantages over IKEv2 in terms of operational reliability. It uses the TCP port 443, the standard HTTPS port, which is universally available and ensures Always On VPN connectivity even behind highly restrictive firewalls.

TLS Certificate

When configuring SSTP, the first thing to consider is the certificate installed on the server. A certificate with an RSA key is most common, but for SSTP, provisioning a certificate with an ECDSA key is recommended for optimal security and performance. See the following two articles regarding SSTP certificate requirements and ECDSA Certificate Signing Request (CSR) creation.

Always On VPN SSL Certificate Requirements for SSTP

Always On VPN ECDSA SSL Certificate Request for SSTP

TLS Configuration

Much like IKEv2, the default TLS security settings for SSTP are less than optimal. However, SSTP can provide excellent security with some additional configuration.

TLS Protocols

There are several deprecated TLS protocols enabled by default in Windows Server. These include SSLv3.0, TLS 1.0, and TLS 1.1. They should be disabled to improve security for TLS. To do this, open an elevated PowerShell window on the VPN server and run the following commands.

New-Item -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 3.0\Server\’ -Force

New-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 3.0\Server\’ -Name Enabled -PropertyType DWORD -Value ‘0’

New-Item -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Server\’ -Force

New-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Server\’ -Name Enabled -PropertyType DWORD -Value ‘0’

New-Item -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Server\’ -Force

New-ItemProperty -Path ‘HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Server\’ -Name Enabled -PropertyType DWORD -Value ‘0’

Cipher Suites

Many weak TLS cipher suites and enabled by default in Windows Server. To further enhance security and performance, they can be optimized using a tool such as IIS Crypto. For example, consider prioritizing cipher suites that use ECDHE and GCM with ECDSA to improve security. Also, remove ciphers that use AES-256 to enhance scalability and performance.

Note: AES-256 does not provide any additional practical security over AES-128. Details here.

PowerShell Script

I have published a PowerShell script on GitHub that performs security hardening and TLS cipher suite optimization to streamline the configuration TLS on Windows Server RRAS servers. You can download the script here.

Validation Testing

After running the script and restarting the server, visit the SSL Labs Server Test site to validate the configuration. You should receive an “A” rating, as shown here.

Note: An “A” rating is not achievable on Windows Server 2012 or Windows Server 2012 R2 when using an RSA TLS certificate. A TLS certificate using ECDSA is required to receive an “A” rating on these platforms.

Additional Information

Always On VPN SSL/TLS Certificate Requirements for SSTP

Always On VPN ECDSA SSL Certificate Request for SSTP

Qualys SSL Labs Server Test Site

Always On VPN Protocol Recommendations for Windows Server RRAS

Microsoft SSTP Specification on MSDN

Always On VPN and IKEv2 Fragmentation

The IKEv2 protocol is a popular choice when designing an Always On VPN solution. When configured correctly it provides the best security compared to other protocols. The protocol is not without some unique challenges, however. IKEv2 is often blocked by firewalls, which can prevent connectivity. Another lesser know issue with IKEv2 is that of fragmentation. This can result in failed connectivity that can be difficult to troubleshoot.

IP Fragmentation

IKEv2 uses UDP for transport, and typically most packets are relatively small. The exception to this is when authentication takes place, especially when using client certificate authentication. The problem is further complicated by long certificate chains and by RSA keys, especially those that are greater than 2048 bit. If the payload exceeds 1500 bytes, the IP packet will have to be broken in to smaller fragments to be sent over the network. If an intermediary device in the path is configured to use a smaller Maximum Transmission Unit (MTU), that device may fragment the IP packets.

IP Fragmentation and Firewalls

Many routers and firewalls are configured to drop IP fragments by default. When this happens, IKEv2 communication may begin initially, but subsequently fail. This typically results in an error code 809 with a message stating the following.

“Can’t connect to [connection name]. The network connection between your computer and the VPN server could not be established because the remote server is not responding. This could be because one of the network devices (e.g. firewalls, NAT, routers, etc.) between your computer and the remote server is not configured to allow VPN connections. Please contact your Administrator or your service provider to determine which device may be causing the problem.”

Always On VPN and IKEv2 Fragmentation

Troubleshooting

When troubleshooting potential IKEv2 fragmentation-related connection failures, a network trace should be taken of the connection attempt on the client. Observe the packet sizes during the conversation, especially IKE_AUTH packets. Packet sizes exceeding the path MTU will have to be fragmented, as shown here.

Always On VPN and IKEv2 Fragmentation

Measuring Path MTU

Measuring the path MTU between the client and server can be helpful when troubleshooting fragmentation related issues. The mtupath.exe utility is an excellent and easy to use tool for this task. The tool can be downloaded here.

Always On VPN and IKEv2 Fragmentation

IKEv2 Fragmentation

To address the challenges with IP fragmentation and potential connectivity issues associated with network devices dropping fragmented packets, the IKEv2 protocol itself can be configured to perform fragmentation at the IKE layer. This eliminates the need for IP layer fragmentation, resulting in better reliability for IKEv2 VPN connections.

Both the server and the client must support IKEv2 fragmentation for this to occur. Many firewall and VPN vendors include support for IKEv2 fragmentation. Consult the vendor’s documentation for configuration guidance. For Windows Server Routing and Remote Access (RRAS) servers, the feature was first introduced in Windows Server 1803 and is supported in Windows Server 2019. Windows 10 clients support IKEv2 fragmentation beginning with Windows 10 1803.

Enabling IKEv2 Fragmentation

Windows 10 clients support IKEv2 fragmentation by default. However, it must be enabled on the server via the registry. The following PowerShell command will enable IKEv2 fragmentation support on Windows Server 1803 and later.

New-ItemProperty -Path “HKLM:\SYSTEM\CurrentControlSet\Services\RemoteAccess\Parameters\Ikev2\” -Name EnableServerFragmentation -PropertyType DWORD -Value 1 -Force

A PowerShell script to implement IKEv2 fragmentation can be found on my GitHub here.

Validation Testing

Once IKEv2 fragmentation is configured on the VPN server, a network capture will reveal the IKE_SA_INIT packet now includes the IKEV2_FRAGMENTATION_SUPPORTED notification message.

Always On VPN and IKEv2 Fragmentation

Additional Information

Windows 10 Always On VPN IKEv2 Security Configuration

RFC 7383 – IKEv2 Message Fragmentation

IEA Software MTU Path Scan Utility

Windows 10 Always On VPN Hands-On Training Classes

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

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