Always On VPN IKEv2 Features and Limitations

Always On VPN IKEv2 Features and LimitationsThe Internet Key Exchange version 2 (IKEv2) VPN protocol is a popular choice for Windows 10 Always On VPN deployments. IKEv2 is a standards-based IPsec VPN protocol with customizable security parameters that allows administrators to provide the highest level of protection for remote clients. In addition, it provides important interoperability with a variety of VPN devices, including Microsoft Windows Server Routing and Remote Access Service (RRAS) and non-Microsoft platforms such as Cisco, Checkpoint, Palo Alto, and others.

IKEv2 Limitations

IKEv2 is clearly the protocol of choice in terms of security. It supports modern cryptography and is highly resistant to interception. It’s not without some operational challenges, however. Consider the following.

Firewalls

IKEv2 uses UDP ports 500 and 4500 for communication. Unfortunately, these ports are not always open. Often, they are blocked by network administrators to prevent users from bypassing security controls or attackers from exfiltrating data.

Fragmentation

IKEv2 packets can become quite large at times, especially when using client certificate authentication with the Protected Extensible Authentication Protocol (PEAP). This can result in fragmentation occurring at the network layer. Unfortunately, many firewalls and network devices are configured to block IP fragments by default. This can result in failed connection attempts from some locations but not others.

Load Balancing

Load balancing IKEv2 connections is not entirely straightforward. Without special configuration, load balancers can cause intermittent connectivity issues for Always On VPN connections. Guidance for configuring IKEv2 load balancing on the Kemp LoadMaster and the F5 BIG-IP can be found here:

IKEv2 Fragmentation

IKEv2 fragmentation can be enabled to avoid IP fragmentation and restore reliable connectivity. IKEv2 fragmentation is supported in Windows 10 and Windows Server beginning with v1803. Guidance for enabling IKEv2 fragmentation on Windows Server RRAS can be found here. Support for IKEv2 fragmentation on non-Microsoft firewall/VPN devices is vendor-specific. Consult with your device manufacturer for more information.

IKEv2 Security and RRAS

Be advised that the default security settings for IKEv2 on Windows Server RRAS are very poor. The minimum recommended security settings and guidelines for implementing them can be found here.

IKEv2 or TLS?

IKEv2 is recommend for deployments where the highest level of security and protection is required for remote connections. In these scenarios, the sacrifice of ubiquitous availability in favor of ultimate security might be desired.

SSTP or another TLS-based VPN protocol is recommended if reliable operation and connectivity are desired. SSTP and TLS VPNs can be configured to provide very good security by following the security and implementation guidelines found here.

IKEv2 with TLS Fallback

In theory, preferring IKEv2 and falling back to the Secure Socket Tunneling Protocol (SSTP) or another TLS-based VPN protocol when IKEv2 is unavailable would seem like a logical choice. This would ensure the highest level of protection, while still providing reliable connectivity. Unfortunately, the Windows VPN client doesn’t work this way in practice. Details here.

Additional Information

Windows 10 Always On VPN IKEv2 Load Balancing with F5 BIG-IP

Windows 10 Always On VPN IKEv2 Load Balancing with Kemp LoadMaster

Windows 10 Always On VPN IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 and SSTP Fallback

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN SSTP Connects then Disconnects

Always On VPN SSTP Connects then DisconnectsWhen Always On VPN clients are configured to use the Secure Socket Tunneling Protocol (SSTP) with Windows Server Routing and Remote Access Service (RRAS), administrators may encounter a scenario in which a client can establish a VPN connection using SSTP successfully, but is then disconnected immediately. The system event log contains an entry with Event ID 6 from the RasSstp source that includes the following error message.

“The SSTP-based VPN connection to the remote access server was terminated because of a security check failure. Security settings on the remote access server do not match settings on this computer. Contact the system administrator of the remote access server and relay the following information.”

Always On VPN Connect and Disconnect with SSTP

Common Causes

The two most common causes of this issue are when SSTP is configured for SSL offload, and when a VPN client is on a network where SSL inspection is taking place.

SSTP Offload

The most common cause of this issue is when SSL offload is configured for SSTP on an external load balancer or application delivery controller (ADC). To prevent interception from a Man-in-the-Middle attack, the VPN client sends the certificate hash of the SSL certificate used when the VPN connection was established. If this information does not match what is configured on the RRAS server, the connection is assumed to be compromised and the connection is immediately dropped.

SSL Inspection

Another scenario where this issue may occur is when a VPN client is behind a network device configured to perform SSL deep-packet inspection (DPI). SSTP VPN clients will be unable to connect to the VPN server in this scenario.

Resolution

When offloading SSL to another device, the RRAS server must be configured to know which SSL certificate is being presented to remote clients. This information is stored in the following registry key.

HKLM:\SYSTEM\CurrentControlSet\Services\SstpSvc\Parameters\SHA256CertificateHash

However, this registry entry requires a binary value, which makes it a challenge to configure manually. To resolve this problem, it is recommended that the same SSL certificate installed on the load balancer/ADC also be installed on the VPN server (even though SSL will be offloaded). To do this, first import the SSL certificate and private key in to the Local Computer certificate store, then open the RRAS management console and perform the following steps.

  1. Right-click the VPN server and choose Properties.
  2. Select the Security tab.
  3. Uncheck Use HTTP in the SSL Certificate Binding section.
  4. Select the appropriate SSL certificate from the Certificate drop-down list (click View to verify).
  5. Click Apply.

This will add the correct SSL certificate information to the registry. Next, re-enable HTTP for SSL offload by performing the following steps.

  1. Check Use HTTP in the SSL Certificate Binding section.
  2. Click Apply.

PowerShell Configuration

If the SSL certificate cannot be installed on the VPN server, or to automate this configuration across multiple servers remotely, download and run the Enable-SstpOffload PowerShell script from my GitHub repository here and run the following command.

Enable-SSTPOffload -CertificateHash [SHA256 Certificate Hash of Public SSL Certificate] -Restart

For example…

Enable-SSTPOffload -CertificateHash “C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2” -Restart

Additional Information

Windows 10 Always On VPN Load Balancing and SSL Offload

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN SSTP Load Balancing and SSL Offload

SSL Certificate Considerations for DirectAccess IP-HTTPSThe Windows Server Routing and Remote Access Service (RRAS) is a popular choice for a VPN server to support Windows 10 Always On VPN deployments. One significant advantage RRAS provides is support for the Secure Socket Tunneling Protocol (SSTP). SSTP is a Microsoft proprietary VPN protocol that uses Transport Layer Security (TLS) to ensure privacy between the VPN client and server. The advantage to using a TLS-based transport is that it leverages the standard HTTPS TCP port 443, making it firewall friendly and ensuring ubiquitous remote access even behind highly restrictive firewalls.

Load Balancing SSTP

Load balancing SSTP can be accomplished in much the same way as a load balancing a common web server using HTTPS. The external load balancer is configured with a virtual IP address (VIP) and each VPN server is configured behind it. Session persistence should be configured to use SSL with source IP address persistence as a fallback.

SSL Offload for SSTP

In most cases, simply forwarding encrypted SSTP connections to the VPN server will be sufficient. However, offloading SSL/TLS processing to an Application Delivery Controller (ADC) or load balancer can be beneficial for the following reasons.

Resource Utilization

Enabling TLS offload for SSTP VPN connections can reduce CPU and memory utilization on the VPN server. However, this will likely only be necessary for very busy servers supporting many concurrent connections.

Security

In some cases, the administrator may not be able to install the public SSL certificate on the VPN server. For example, a security policy may exist that restricts SSL certificate installation to dedicated security devices using a Hardware Security Module (HSM). In some cases, it may be desirable to restrict access to high value certificates such as wildcard certificates.

Certificate Management

Often SSL certificates are implemented on load balancers to reduce certificate sprawl and to ease the management and administration burden in the enterprise. By having all enterprise certificates installed only on dedicated security devices, administrators can more effectively monitor and manage SSL certificate lifecycles.

SSTP Configuration for TLS Offload

Configuration changes must be made on the load balancer and the RRAS server to support TLS offload for SSTP.

Load Balancer

Install the public SSL certificate on the load balancer and configure it for TLS termination. Configure the load balancer to then use HTTP for backend server connections. Consult the load balancer vendor’s documentation for configuration guidance.

RRAS Server

If the public SSL certificate is installed on the VPN server, enabling TLS offload for SSTP is simple and straightforward. Follow the steps below to enable TLS offload for SSTP VPN connections.

  1. Open the RRAS management console (rrasmgmt.msc).
  2. Right-click the VPN server and choose Properties.
  3. Select the Security tab.
  4. Check Use HTTP in the SSL Certificate Binding section.
  5. Click Ok and then Yes to restart the Remote Access service.

Always On VPN SSTP Load Balancing and SSL Offload

If the public SSL certificate is not or cannot be installed on the RRAS server, additional configuration will be required. Specifically, SSL offload for SSTP must be configured using the Enable-SSTPOffload PowerShell script, which can be downloaded here.

Once the script has been downloaded and imported, open an elevated PowerShell command window and enter the following command.

Enable-SSTPOffload -CertificateHash [SHA256 Certificate Hash of Public SSL Certificate] -Restart

For example…

Enable-SSTPOffload -CertificateHash “C3AB8FF13720E8AD9047DD39466B3C8974E592C2FA383D4A3960714CAEF0C4F2” -Restart

Additional Information

Windows 10 Always On VPN SSL Certificate Requirements for SSTP

Windows 10 Always On VPN IKEv2 and SSTP Fallback

Windows 10 Always On VPN Hands-On Training Classes for 2019

Troubleshooting Always On VPN Error Code 809

When testing an Always On VPN connection, the administrator may encounter a scenario where the VPN client fails to connect to the VPN server. On the Windows 10 client the error message states 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

In addition, the Application event log records an error message with Event ID 20227 from the RasClient source. The error message states the following.

“The User [username] dialed a connection named [connection name] with has failed. The error code returned on failure is 809.”

Troubleshooting Always On VPN Error Code 809

Connection Timeout

The error code 809 indicates a VPN timeout, meaning the VPN server failed to respond. Often this is related directly to network connectivity, but sometimes other factors can come in to play.

Troubleshooting VPN Error Code 809

When troubleshooting VPN error code 809 the following items should be carefully checked.

  • Name Resolution – Ensure the VPN server’s public hostname resolves to the correct IP address.
  • Firewall Configuration – Confirm the edge firewall is configured properly. Inbound TCP port 443 is required for the Secure Socket Tunneling Protocol (SSTP) and inbound UDP ports 500 and 4500 are required for the Internet Key Exchange version 2 (IKEv2) protocol. Make sure that any NAT rules are forwarding traffic to the correct server.
  • Load Balancer Configuration – If VPN servers are located behind a load balancer, make certain that virtual IP address and ports are configured correctly and that health checks are passing. For IKEv2 specifically, it is crucial that UDP ports 500 and 4500 be delivered to the same backend server. This commonly requires custom configuration. For example, on the KEMP LoadMaster the administrator will configure “port following”. On the F5 BIG-IP a  custom “persistence profile” must be configured. On the Citrix NetScaler a “persistency group” must be defined.

IKEv2 Fragmentation

VPN error code 809 can also be caused by IKE fragmentation when using the IKEv2 VPN protocol. During IKEv2 connection establishment, payload sizes may exceed the IP Maximum Transmission Unit (MTU) for the network path between the client and server. This causes the IP packets to be fragmented. However, it is not uncommon for intermediary devices (routers, NAT devices, or firewalls) to block IP fragments. When this occurs, a VPN connection cannot be established. However, looking at a network trace of the connection attempt, the administrator will see that the connection begins but subsequently fails.

Troubleshooting Always On VPN Error Code 809

Enable IKEv2 Fragmentation Support

The IKEv2 protocol includes support for fragmenting packets at the IKE layer. This eliminates the need for fragmenting packets at the IP layer. IKEv2 fragmentation must be configured on both the client and server.

Client

IKEv2 fragmentation was introduced in Windows 10 1803 and is enabled by default. No client-side configuration is required.

Server

IKEv2 is commonly supported on many firewall and VPN devices. Consult the vendor’s documentation for configuration guidance. For Windows Server Routing and Remote Access (RRAS) servers, IKEv2 fragmentation was introduced in Windows Server 1803 and is also supported in Windows Server 2019. It is enabled via a registry key. The following PowerShell command can be used to enable IKEv2 fragmentation on supported servers.

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

Validation

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 and IKEv2 Fragmentation

Windows 10 Always On VPN IKEv2 Security Configuration

Windows 10 Always On VPN Hands-On Training Classes

Always On VPN IKEv2 Connection Failure Error Code 800

Always On VPN administrators may encounter a scenario in which Windows 10 clients are unable to establish an IKEv2 VPN connection to a Windows Server Routing and Remote Access Service (RRAS) server or a third-party VPN device under the following conditions.

  1. The VPN connection is configured using ProfileXML.
  2. ProfileXML includes the <CryptographySuite> element.
  3. The VPN server is configured to use a custom IPsec policy.
  4. The VPN server supports only IKEv2.
  5. The <NativeProtocolType> in ProfileXML is set to Automatic.

When these specific conditions are met, the client will be unable to connect to the VPN server using IKEv2. The error message states:

The remote connection was not made because the attempted VPN tunnels failed. The VPN server might be unreachable. If this connection is attempting to use an L2TP/IPsec tunnel, the security parameters required for IPsec negotiation might not be configured properly.

Always On VPN IKEv2 VPN Connection Failure Error Code 800

In addition, the event log will include an error message from the RasClient source with event ID 20227 that includes the following error message.

The user [username] dialed a connection named [connection name] which has failed. The error code returned on failure is 800.

Always On VPN IKEv2 VPN Connection Failure Error Code 800

A manually configured VPN connection using IKEv2 will connect successfully under these same conditions, however.

IKEv2 Error Code 800

Error code 800 translates to ERROR_AUTOMATIC_VPN_FAILED, which is somewhat ambiguous. The error description is:

Unable to establish the VPN connection. The VPN server may be unreachable, or security parameters may not be configured properly for this connection.

Digging Deeper

A network trace of the IKEv2 VPN connection reveals the true source of the problem, which is a failure of the client and server to successfully negotiate an IKEv2 security association (SA). During the SA initiation process, the parameters offered by the client are unacceptable to the server, resulting in a NO_PROPOSAL_CHOSEN notification being returned by the server.

Always On VPN IKEv2 VPN Connection Failure Error Code 800

Custom Cryptography Settings Ignored

It appears that the Always On VPN connection ignores the custom cryptography settings defined in the CryptographySuite element in ProfileXML. However, this only occurs when the NativeProtocolType is set to Automatic. Presumably, this is a bug. 🙂

Workaround

As a workaround, set the NativeProtocolType to IKEv2. When NativeProtocolType is set to IKEv2, the VPN connection recognizes the IKEv2 parameters defined in the CryptographySuite element and the VPN connection will be established successfully.

Additional Information

Always On VPN IKEv2 Security Configuration

Always On VPN Certificate Requirements for IKEv2

Always On VPN IKEv2 Load Balancing with the 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.

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

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

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

Always On VPN Protocol Recommendations for Windows Server Routing and Remote Access Service (RRAS)Windows 10 Always On VPN is infrastructure independent and can be implemented using third-party VPN devices. It is not necessary to deploy any Windows servers at all to support an Always On VPN solution. However, in a recent blog post I outlined some compelling reasons to consider using Windows Server 2016’s Routing and Remote Access Service (RRAS) feature to terminate VPN connections. RRAS supports both modern and legacy VPN protocols, each with their own advantages and disadvantages. The choice of which protocols to support will be determined by many factors, but it is important to understand the capabilities of each to make an informed decision.

RRAS VPN Protocols

Windows RRAS supports the following VPN protocols.

  • Internet Key Exchange version 2 (IKEv2) – RFC7296
  • Secure Sockets Tunneling Protocol (SSTP) – Microsoft
  • Layer Two Tunneling Protocol over IPsec (L2TP/IPsec) – RFC2661
  • Point-to-Point Tunneling Protocol (PPTP) – RFC2637

There are pros and cons associated with each of these VPN protocols. Here’s a breakdown of each.

IKEv2

This IPsec-based VPN protocol is the preferred choice for most deployments. IKEv2 provides the best security and performance, with native features that enhance mobility. This latest version of IKE (v2) features streamlined messaging during connection establishment and enhanced session management that reduce protocol overhead and improve performance.

Advantages: Best security and performance.
Disadvantages: Firewalls may block required UDP ports.

SSTP

SSTP is an excellent alternative to IKEv2. It uses industry standard Transport Layer Security (TLS), making it widely accessible from most locations. It provides good security out of the box, but can be improved upon with additional configuration. SSTP lends itself well to load balancing, making it much easier to scale out than IKEv2. Optionally, TLS can be offloaded to an Application Delivery Controller (ADC) to reduce resource utilization on the RRAS server and further improve performance.

Advantages: Easy to configure with firewall friendly access.
Disadvantages: Not as secure IKEv2.

L2TP

While technically supported for Always On VPN, L2TP is a legacy VPN protocol that offers no real advantages over IKEv2. Its use is unnecessary and should be avoided.

Advantages: None.
Disadvantages: Firewalls may block required UDP ports.

PPTP

PPTP is considered an obsolete VPN protocol with many known security vulnerabilities. Its use should be avoided at all costs.

Advantages: None.
Disadvantages: Insecure.

Summary

Implementation best practices dictate that IKEv2 and SSTP be enabled to support Windows 10 Always On VPN connections when using Windows Server 2016 RRAS. The use of L2TP/IPsec and PPTP should be avoided. The combination of IKEv2 and SSTP will provide the best security and availability for remote workers. Clients that can establish IKEv2 VPN connections can take advantages of the security and performance benefits it provides. SSTP can be enabled as a fallback for clients that are unable to establish an IKEv2 connection due to restricted firewall access.

Always On VPN Hands-On Training

Interested in learning more about Windows 10 Always On VPN? Hands-on training classes are now forming. More details here.

Additional Resources

Frequently Asked Questions about Microsoft’s PPTP Implementation

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

Windows 10 Always On VPN and the Future of DirectAccess 

5 Things DirectAccess Administrators Should Know about Always On VPN 

3 Important Advantages of Windows 10 Always On VPN over DirectAccess 

Windows 10 Always On VPN Hands-On Training Classes

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

Windows 10 Always On VPN hands-on training classes now forming. Details here.

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

As I’ve written about in the past, Windows 10 Always On VPN has many advantages over DirectAccess. One of the most important features is that Always On VPN is completely infrastructure independent. Always On VPN is implemented entirely on the client side, so there is no reliance on Windows infrastructure servers at all. In theory, you could deploy an Always On VPN solution using an entirely third-party backend infrastructure. This is crucial because many organizations already have security infrastructure in place today. However, there are still some compelling reasons to choose Windows Server 2016 as the VPN server to support Windows 10 Always On VPN.

Considerations for Windows Server

Windows Server 2016 includes a very capable VPN server in the Routing and Remote Access Service (RRAS) role. Using Windows Server 2016 RRAS will meet the requirements for many deployment scenarios. RRAS also provides some unique advantages too. The following are some important considerations for choosing RRAS for VPN.

Easy to Deploy

The RRAS role in included in all Windows server network operating systems and can be enabled easily using the GUI or PowerShell. RRAS is mature and well-documented, making installation and configuration simpler. In fact, all of the Microsoft Windows 10 Always On VPN documentation guidance references RRAS.

Reduced Costs

No investment in proprietary hardware is required, because RRAS runs on Windows Server 2016 and can be deployed on existing virtual infrastructure. Deploying additional RRAS virtual machines enables quick and efficient scaling up of the solution without the need to deploy additional expensive hardware. Importantly, RRAS requires no additional per-client or per-device licensing. In addition, RRAS can be managed using existing Windows administration skill sets and does not require dedicated, and often expensive solution-specific expertise.

Modern Protocol Support

RRAS includes support for modern VPN protocols such as Internet Key Exchange version 2 (IKEv2) and Secure Socket Tunneling Protocol (SSTP). IKEv2 is the protocol of choice or most deployments, and is required for supporting the device tunnel. SSTP is a firewall-friendly protocol that ensures remote Windows clients can connect from anywhere. Layer Two Tunneling Protocol over IPsec (L2TP/IPsec) and Point-to-Point Tunneling Protocol (PPTP) are also supported for legacy client compatibility.

Summary

Although Windows 10 Always On VPN can be implemented using third-party VPN servers, it’s important not to overlook Windows server either. Windows Server 2016 RRAS has some important advantages over third-party infrastructure. RRAS is mature and well understood, with an abundance of published documentation available. Leveraging RRAS eliminates the need for costly proprietary hardware and client licensing, while at the same time reducing administrative overhead and streamlining support. RRAS also includes native support for modern VPN protocols, ensuring reliable client connectivity from any location.

Additional Resources

3 Important Advantages of Windows 10 Always On VPN over DirectAccess 

Windows 10 Always On VPN and the Future of DirectAccess 

5 Things DirectAccess Administrators Should Know About Always On VPN 

 

 

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