Always On VPN IKEv2 Security Configuration

Always On VPN IKEv2 Security ConfigurationWhen deploying Windows 10 Always On VPN, many administrators choose the Internet Key Exchange version 2 (IKEv2) protocol to provide the highest level of security and protection for remote connections. However, many do not realize the default security parameters for IKEv2 negotiated between a Windows Server running the Routing and Remote Access Service (RRAS) and a Windows 10 VPN client are far less than ideal from a security perspective. Additional configuration on both the server and the client will be required to ensure adequate security and protection for IKEv2 VPN connections.

Windows 10 and RRAS IKEv2 Defaults

In their default configuration, a Windows 10 client connecting to a Windows Server running RRAS will negotiate an IKEv2 VPN connection using the following IPsec security parameters.

  • Encryption: 3DES
  • Authentication/Integrity: SHA-1
  • Key Size: DH Group 2 (1024 bit)

This information can be obtained by opening an elevated PowerShell command window and running the following command.

Get-NetIPsecMainModeSA | Select-Object -First 1

Always On VPN IKEv2 Security Configuration

This can also be confirmed by viewing a network trace as shown here.

Always On VPN IKEv2 Security Configuration

These IPsec security parameters might have been acceptable in the 90’s, but they certainly are not today. 🙂

Improving IKEv2 Security

To provide a baseline level of protection to meet today’s requirements for security and privacy for IKEv2 VPN connections, the following are the minimum recommended IPsec security parameters.

  • Encryption: AES128
  • Authentication/Integrity: SHA-256
  • Key Size: DH Group 14 (2048 bit)

RRAS Custom IPsec Policy

To implement these recommended security baselines for IKEv2 on a Windows Server running RRAS it will be necessary to define a custom IPsec security policy. To do this, open an elevated PowerShell command window and run the following commands on each RRAS server.

Set-VpnServerConfiguration -CustomPolicy -AuthenticationTransformConstants SHA256128 -CipherTransformConstants AES128 -DHGroup Group14 -EncryptionMethod AES128 -IntegrityCheckMethod SHA256 -PFSgroup PFS2048 -SADataSizeForRenegotiationKilobytes 102400

Restart the Remote Access Management service for the changes to take effect.

Restart-Service RemoteAccess -PassThru

Always On VPN IKEv2 Security Configuration

Windows 10 Client Settings

The IPsec policy must match on both the server and the client for an IKEv2 VPN connection to be successful. Unfortunately, none of the IKEv2 IPsec security association parameters proposed by default on Windows 10 clients use 2048-bit keys (DH Group 14), so it will be necessary to define a custom IPsec security policy on the client to match the settings configured on the server.

To configure a matching IPsec security policy on an individual Windows 10 VPN client, open an elevated PowerShell command window and run the following command.

$connection = “[connection name]”
Set-VpnConnectionIPsecConfiguration -ConnectionName $connection -AuthenticationTransformConstants SHA256128 -CipherTransformConstants AES128 -DHGroup Group14 -EncryptionMethod AES128 -IntegrityCheckMethod SHA256 -PFSgroup PFS2048 -Force

Always On VPN IKEv2 Security Configuration

Restore Defaults

In the process of testing it may be necessary to restore the default IKEv2 configuration on both the client and the server. This can be accomplished by running the following PowerShell commands.

Server – Set-VpnServerConfiguration -RevertToDefault

Client – Set-VpnConnectionIPsecConfiguration -ConnectionName [connection_name] -RevertToDefault -Force

Always On VPN XML Settings

To implement a custom IPsec policy using the minimum recommended security settings for an Always On VPN connection using IKEv2, add the following settings to your ProfileXML.

<VPNProfile>
 <NativeProfile>
  <CryptographySuite>
   <AuthenticationTransformConstants>SHA256128</AuthenticationTransformConstants>
   <CipherTransformConstants>AES128</CipherTransformConstants>
   <EncryptionMethod>AES128</EncryptionMethod>
   <IntegrityCheckMethod>SHA256</IntegrityCheckMethod>
   <DHGroup>Group14</DHGroup>
   <PfsGroup>PFS2048</PfsGroup>
  </CryptographySuite>
 </NativeProfile>
</VPNProfile>

Why Not AES 256?

In the examples above you’ll notice that I’ve chosen to use AES128 and not AES256. This is by design, as AES256 does not provide any practical additional security in most use cases. Details here.

Enhanced Security and Performance

To further improve security and performance for IKEv2, consider implementing Elliptic Curve Cryptography (EC) certificates and using Galois Counter Mode (GCM) cipher suites such as GCMAES128 for authentication and encryption.

Additional Information

Always On VPN Certificate Requirements for IKEv2

Always On VPN IKEv2 Connection Failure Error Code 800

Always On VPN IKEv2 Load Balancing with the KEMP LoadMaster Load Balancer

Always On VPN and Windows Server 2019 NPS Bug

Note: This post updated March 19,2019 to reflect new workaround configuration guidance.

When deploying a Windows Server 2019 Network Policy Server (NPS) to support a Windows 10 Always On VPN implementation, administrators may encounter the following error when attempting to establish a VPN connection on a remote Windows 10 client.

Can’t connect to [connection name].

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. Please contact the Administrator of the RAS server and notify them of this error.

Always On VPN and Windows Server 2019 Network Policy Server Bug
In addition, an event ID 20227 from the RasClient will be recorded in the application event log with the following error message.

The user [username] dialed a connection named [connection name] which has failed. The error code returned on failure is 812.

Always On VPN and Windows Server 2019 Network Policy Server Bug

Common Causes

Always On VPN error code 812 indicates an authentication policy mismatch between the client and the server. This often occurs when, for example, the server is configured to use Protected Extensible Authentication Protocol (PEAP), but the client is configured to use Microsoft CHAP Version 2 (MS-CHAP v2).

Troubleshooting

Carefully review the authentication policy on both the client and server to ensure they match. Next, enable firewall logging on the NPS server to log both allowed and dropped packets. Attempt another VPN connection and observe the firewall logs. In this example the firewall is dropping packets inbound on UDP port 1812.

Always On VPN and Windows Server 2019 Network Policy Server Bug

Interestingly, the default Windows firewall rule allowing inbound UDP port 1812 is enabled and set to allow for all profiles.

Always On VPN and Windows Server 2019 Network Policy Server Bug

Windows Server 2019 Bug

It appears that Microsoft’s recently released Windows Server 2019 has a bug that prevents NPS from working correctly out of the box. Specifically, it looks like the default Windows firewall rules to allow inbound UDP port 1812 (RADIUS authentication) and inbound UDP port 1813 (RADIUS accounting) do not work.

Resolution

To resolve this issue, open an elevated command window and enter the following command.

sc sidtype IAS unrestricted

Once complete, restart the server and the default Windows Firewall rules for NPS traffic will work correctly.

Additional Information

Windows 10 Always On VPN NPS Load Balancing Strategies

Comparing DirectAccess and NetMotion Mobility – Australia and New Zealand

Australia and New Zealand! Comparing DirectAccess and NetMotion Mobility free live webinar Thursday, November 29 at 10:00AM AEDT. Register here!

DirectAccess on Windows Server 2016 CoreFor many years, DirectAccess has been the gold standard for enterprise remote access. Its seamless and transparent operation improves productivity for mobile workers, and since it is always on, administrators enjoy improved visibility and management for their field-based assets.

As incredible as DirectAccess is, it is not without its limitations. For example, DirectAccess works only with Windows Enterprise edition clients that are joined to the domain. Professional Edition and non-domain joined machines are not supported. It also lacks many of the security features enterprise organizations require, such as device health checks and granular network access. In addition, DirectAccess communication is complex, with many different layers of encapsulation, authentication, and encryption. High protocol overhead can lead to poor performance over high latency or low bandwidth connections.

NetMotion Mobility as an Alternative to DirectAccessNetMotion Mobility is a secure remote access solution that is an excellent alternative to DirectAccess. It provides the same seamless, transparent, always on remote connectivity that DirectAccess provides, while at the same time offering much more in terms of features and capabilities. It supports a much broader range of clients, includes native Network Access Control (NAC) and application filtering, and offers enhanced performance.

To learn more about NetMotion Mobility, join me on Thursday, November 29 at 10:00AM AEDT (UTC +11) for a free live webinar with NetMotion. I’ll provide an overview of NetMotion Mobility and how it compares with DirectAccess. I’ll also demonstrate how it can help overcome some of the inherent limitations of DirectAccess too. Register today!

DirectAccess and NetMotion Mobility Webinar

Always On VPN Device Tunnel Missing in Windows 10 UI

Always On VPN Device Tunnel Missing in Windows 10 UIUnlike DirectAccess, Always On VPN connections are provisioned to the user, not the machine. Beginning with Windows 10 release 1709 Microsoft introduced the device tunnel option to provide feature parity with DirectAccess. The device tunnel provides pre-logon network connectivity to support important deployment scenarios such as logging on without cached credentials and unattended remote systems management.

Device Tunnel Configuration

Guidance for creating and deploying a device tunnel connection can be found here. It’s important to note that the device tunnel is always on by default. Also, there can only be a single device tunnel configured per device. You must remove an existing device tunnel before configuring a new one.

Known Issues

After configuring a Windows 10 Always On VPN device tunnel the administrator may notice two anomalies. First, the device tunnel is missing in the Windows UI after it is created. Second, viewing the status of the device tunnel connection using PowerShell indicates the connection is “disconnected” even though it is connected.

Device Tunnel Missing

As you can see below, event though both a device and user tunnel have been provisioned, the Windows UI reports only a single Always On VPN connection, that being the user connection.

Always On VPN Device Tunnel Missing in Windows 10 UI

However, the device tunnel does appear in the Network Connections control panel applet (ncpa.cpl), as shown here.

Always On VPN Device Tunnel Missing in Windows 10 UI

This is expected and by design. The device tunnel is not displayed to the user in the Windows UI as it is provisioned to the machine, not the user. It appears on the Control Panel because the applet is capable of enumerating both user and system connections.

Device Tunnel Disconnected

The status of the Windows 10 Always On VPN device tunnel connection can be viewed by running the Get-VpnConnection -AllUserConnection PowerShell command. However, at the time of this writing, PowerShell always reports the connection status as “Disconnected”. This appears to be a bug; one which Microsoft is hopefully working to address.

Always On VPN Device Tunnel Missing in Windows 10 UI

Summary

The Windows 10 Always On VPN device tunnel option allows administrators to enable scenarios previously supported with DirectAccess, including logging on without cached credentials and unattended remote support. Not all deployments require a device tunnel, but it is an important option available to administrators to address specific use cases.

Additional Information

Windows 10 Always On VPN Device Tunnel Configuration using PowerShell

Windows 10 Always On VPN RasMan Device Tunnel Failure

Deleting a Windows 10 Always On VPN Device Tunnel

 

Troubleshooting Always On VPN Error Code 0x80092013

Troubleshooting Always On VPN Error Code 0x80092013Windows Server Routing and Remote Access Service (RRAS) is commonly used for Windows 10 Always On VPN deployments because it is easy to configure and manage and it includes Microsoft’s proprietary Secure Socket Tunneling Protocol (SSTP). SSTP is a Transport Layer Security (TLS) VPN protocol that is firewall-friendly and ubiquitously available. However, a common configuration mistake can lead to failed connections.

Error 0x80092013

A Windows 10 Always On VPN client may fail to establish a VPN connection to an RRAS VPN server when using SSTP. The VPN client will return the following error message.

“Can’t connect to Always On VPN. The revocation function was unable to check revocation because the revocation server was offline.”

Troubleshooting Always On VPN Error Code 0x80092013

The event log will also include RasClient event ID 20227 with the following error.

“The user [domain\user] dialed a connection named [connection name] which has failed. The error code returned on failure is -2146885613.”

Troubleshooting Always On VPN Error Code 0x80092013

The Win32 error code –2146885613 converts to hexadecimal 0x80092013, which translates to CRYPT_E_REVOCATION_OFFLINE, indicating that the client was unable to successfully perform a check of the VPN server’s SSL certificate.

Revocation Checking

When the VPN client attempts to establish an SSTP connection to the Windows RRAS VPN, it will check the Certification Revocation List (CRL) using the information provided in the SSL certificate. If the CRL is unreachable for any reason, the client will not complete the connection

Common Cause of Error 0x80092013

Certificate revocation failures for Windows 10 Always On VPN SSTP connections commonly occur when the RRAS VPN server is configured with an SSL certificate issued by an internal certification authority (CA) and the CRL is not publicly available.

Resolving Error 0x80092013

Making the internal CA’s CRL available publicly will of course resolve this error. However, best practice recommendations for the SSTP SSL certificate call for the use of a certificate issued by a public CA. For detailed information about SSL certificate requirements and recommendations, please see Always On VPN SSL Certificate Requirements for SSTP.

Additional Information

Always On VPN SSL Certificate Requirements for SSTP

Always On VPN ECDSA SSL Certificate Request for SSTP

Always On VPN Protocol Recommendations for Windows RRAS

Always On VPN ECDSA SSL Certificate Request for SSTP

As I’ve discussed previously, it is strongly recommended that the TLS certificate used for SSTP be signed using the Elliptic Curve Digital Signature Algorithm (ECDSA). ECDSA provides better security and performance compared to RSA certificates for Windows 10 Always On VPN connections using SSTP. See my previous post Always On VPN SSL Certificate Requirements for SSTP for more information.

Certificate Signing Request

To generate a Certificate Signing Request (CSR) using ECDSA to send to a public Certification Authority (CA), open the local computer certificate store (certlm.msc) on any Windows server or client and follow the steps below.

  1. Expand Certificates – Local Computer.
  2. Right-click the Personal folder and choose All Tasks > Advanced Operations > Create Custom Request.
  3. Click Next.
  4. Select Proceed without enrollment policy.
  5. Click Next.
  6. From the Template drop-down list choose (No template) CNG key.
  7. Click Next.
  8. Click Details.Always On VPN ECDSA SSL Certificate Request for SSTP
  9. Click Properties.
  10. On the General tab enter a name in the Friendly name field.
  11. Click on the Subject tab.
    1. In the Subject name section, from the Type drop-down list choose Common name.
    2. In the Value field enter the VPN server’s public hostname and click Add.
    3. In the Alternative name section, from the Type drop-down list choose DNS.
    4. In the Value field enter the VPN server’s public hostname and click Add.Always On VPN ECDSA SSL Certificate Request for SSTP
  12. Click on the Extensions tab.
    1. Expand Extended Key Usage (application policies).
    2. Highlight Server Authentication.
    3. Click Add.Always On VPN ECDSA SSL Certificate Request for SSTP
  13. Click on the Private Key tab.
    1. Expand Cryptographic Service Provider.
    2. Uncheck RSA,Microsoft Software Key Storage Provider.
    3. Check ECDSA_P256,Microsoft Software Key Storage Provider.Always On VPN ECDSA SSL Certificate Request for SSTP
  14. Expand Key options.
    1. Select the option to Make private key exportable.Always On VPN ECDSA SSL Certificate Request for SSTP
  15. Click Ok.
  16. Click Next.
  17. Enter a name for the file in the File Name field.
  18. Click Finish.

Submit the Request

Once complete, submit the CSR for signing to your favorite public CA. Based on my experience, some CAs are easier to obtain ECDSA-signed certificates than other. Today, Digicert seems to be one of the better public CAs for obtaining EC TLS certificates.

Complete the Request

Once the CA has issued the certificate, import the certificate in to the local computer certificate store on the same client or server where the original CSR was created. The certificate can then be exported and imported on additional VPN servers, if required.

Additional Information

Always On VPN SSL Certificate Requirements for SSTP

Always On VPN Protocol Recommendations for RRAS

 

Always On VPN Multisite with Azure Traffic Manager

Always On VPN Multisite with Azure Traffic ManagerEliminating single points of failure is crucial to ensuring the highest levels of availability for any remote access solution. For Windows 10 Always On VPN deployments, the Windows Server 2016 Routing and Remote Access Service (RRAS) and Network Policy Server (NPS) servers can be load balanced to provide redundancy and high availability within a single datacenter. Additional RRAS and NPS servers can be deployed in another datacenter or in Azure to provide geographic redundancy if one datacenter is unavailable, or to provide access to VPN servers based on the location of the client.

Multisite Always On VPN

Unlike DirectAccess, Windows 10 Always On VPN does not natively include support for multisite. However, enabling multisite geographic redundancy can be implemented using Azure Traffic Manager.

Azure Traffic Manager

Traffic Manager is part of Microsoft’s Azure public cloud solution. It provides Global Server Load Balancing (GSLB) functionality by resolving DNS queries for the VPN public hostname to an IP address of the most optimal VPN server.

Advantages and Disadvantages

Using Azure Traffic manager has some benefits, but it is not with some drawbacks.

Advantages – Azure Traffic Manager is easy to configure and use. It requires no proprietary hardware to procure, manage, and support.

Disadvantages – Azure Traffic Manager offers only limited health check options. Azure Traffic Manager’s HTTPS health check only accepts HTTP 200 OK responses as valid. Most TLS-based VPNs will respond with an HTTP 401 Unauthorized, which Azure Traffic Manager considers “degraded”. The only option for endpoint monitoring is a simple TCP connection to port 443, which is a less accurate indicator of endpoint availability.

Note: This scenario assumes that RRAS with Secure Socket Tunneling Protocol (SSTP) or another third-party TLS-based VPN server is in use. If IKEv2 is to be supported exclusively, it will still be necessary to publish an HTTP or HTTPS-based service for Azure Traffic Manager to monitor site availability.

Traffic Routing Methods

Azure Traffic Manager provide four different methods for routing traffic.

Priority – Select this option to provide active/passive failover. A primary VPN server is defined to which all traffic is routed. If the primary server is unavailable, traffic will be routed to another backup server.

Weighted – Select this option to provide active/active failover. Traffic is routed to all VPN servers equally, or unequally if desired. The administrator defines the percentage of traffic routed to each server.

Performance – Select this option to route traffic to the VPN server with the lowest latency. This ensures VPN clients connect to the server that responds the quickest.

Geographic – Select this option to route traffic to a VPN server based on the VPN client’s physical location.

Configure Azure Traffic Manager

Open the Azure management portal and follow the steps below to configure Azure Traffic Manager for multisite Windows 10 Always On VPN.

Create a Traffic Manager Resource

  1. Click Create a resource.
  2. Click Networking.
  3. Click Traffic Manager profile.

Create a Traffic Manager Profile

  1. Enter a unique name for the Traffic Manager profile.
  2. Select an appropriate routing method (described above).
  3. Select a subscription.
  4. Create or select a resource group.
  5. Select a resource group location.
  6. Click Create.

Always On VPN Multisite with Azure Traffic Manager

Important Note: The name of the Traffic Manager profile cannot be used by VPN clients to connect to the VPN server, since a TLS certificate cannot be obtained for the trafficmanager.net domain. Instead, create a CNAME DNS record that points to the Traffic Manager FQDN and ensure that name matches the subject or a Subject Alternative Name (SAN) entry on the VPN server’s TLS and/or IKEv2 certificates.

Endpoint Monitoring

Open the newly created Traffic Manager profile and perform the following tasks to enable endpoint monitoring.

  1. Click Configuration.
  2. Select TCP from the Protocol drop-down list.
  3. Enter 443 in the Port field.
  4. Update any additional settings, such as DNS TTL, probing interval, tolerated number of failures, and probe timeout, as required.
  5. Click Save.

Always On VPN Multisite with Azure Traffic Manager

Endpoint Configuration

Follow the steps below to add VPN endpoints to the Traffic Manager profile.

  1. Click Endpoints.
  2. Click Add.
  3. Select External Endpoint from the Type drop-down list.
  4. Enter a descriptive name for the endpoint.
  5. Enter the Fully Qualified Domain Name (FQDN) or the IP address of the first VPN server.
  6. Select a geography from the Location drop-down list.
  7. Click OK.
  8. Repeat the steps above for any additional datacenters where VPN servers are deployed.

Always On VPN Multisite with Azure Traffic Manager

Summary

Implementing multisite by placing VPN servers is multiple physical locations will ensure that VPN connections can be established successfully even when an entire datacenter is offline. In addition, active/active scenarios can be implemented, where VPN client connections can be routed to the most optimal datacenter based on a variety of parameters, including current server load or the client’s current location.

Additional Information

Windows 10 Always On VPN Hands-On Training Classes

Always On VPN Hands On Training Classes Coming to Dallas and San Francisco

Windows 10 Always On VPN Hands-On Training Classes for 2018Two more dates for my popular three-day Windows 10 Always On VPN Hands-On Training classes have been added to the schedule for 2018! Classes are now forming in Dallas, October 23-25 and in San Francisco, November 13-15, 2018. These training classes will cover all aspects of designing, implementing, and supporting an Always On VPN solution in the enterprise. The following topics will be covered in detail.

  • Windows 10 Always On VPN overview
  • Introduction to CSP
  • Infrastructure requirements
  • Planning and design considerations
  • Installation, configuration, and client provisioning

Advanced topics will include…

  • Redundancy and high availability+
  • Cloud-based deployments
  • Third-party VPN infrastructure and client support
  • Multifactor authentication
  • Always On VPN migration strategies

Windows 10 Always On VPN Hands-On Training Classes for 2018

Register Today

Reservations are being accepted now! The cost for this 3-day hands-on training class is $4995.00 USD. Space is limited, so don’t wait to register! Fill out the form below to save your seat now.

Group discounts are available! Private training sessions for large organizations are also available upon request.

Always On VPN Routing Configuration

Windows 10 Always On VPN Routing ConfigurationWhen configuring Windows 10 Always On VPN, the administrator must choose between force tunneling and split tunneling. When force tunneling is used, all network traffic from the VPN client is routed over the VPN tunnel. When split tunneling is used, the VPN client must be configured with the necessary IP routes to establish remote network connectivity to on-premises resources. How those routes are established is a common source of confusion. This article provides guidance for properly configuring routing for Always On VPN clients.

Class Based Routing

IP addresses are assigned to Windows 10 Always On VPN clients from either a static pool of addresses configured by the administrator or by DHCP. If split tunneling is enabled, the client will also be assigned a class-based route that is derived from the IP address assigned to it by the VPN server, by default. If the client is assigned an IP address from the Class A network, a corresponding /8 prefix is used. For Class B networks a /16 prefix is defined, and for Class C networks a /24 prefix is used.

As an example, if the VPN server assigns the client an IP address of 10.21.12.103, a route to the 10.0.0.0/8 network is added to the client’s routing table, as shown here.

Windows 10 Always On VPN Routing Configuration

Complex Networks

This default class-based route is of limited use though, and is only applicable when the internal network is simple and VPN clients are assigned IP addresses from the same subnet class. In the example above, if the entire internal network resides in the 10.0.0.0/8 Class A address space, all resources will be reachable by the VPN client. Any resources in the Class B or Class C subnet ranges would be unreachable without additional configuration.

Route Configuration

To configure routing for Windows 10 Always On VPN clients, first disable the default class-based route by defining the following element in ProfileXML as shown here.

<VPNProfile>
   <NativeProfile>
      <DisableClassBasedDefaultRoute>true</DisableClassBasedDefaultRoute>
   </NativeProfile>
</VPNProfile>

Next, enable specific routes as needed by defining the following element(s) in ProfileXML. The example below defines routes for all private RFC 1918 networks.

<VPNProfile>
   <Route>
      <Address>10.0.0.0</Address>
      <PrefixSize>8</PrefixSize>
   </Route>
   <Route>
      <Address>172.16.0.0</Address>
      <PrefixSize>12</PrefixSize>
   </Route>
   <Route>
      <Address>192.168.0.0</Address>
      <PrefixSize>16</PrefixSize>
   </Route>
</VPNProfile>

Once implemented, the VPN client’s routing table will appear as shown here.

Windows 10 Always On VPN Routing Configuration

Summary

Proper routing is crucial for ensuring full network connectivity and access to internal resources for Windows 10 Always On VPN clients. When split tunneling is employed, avoid using the default class-based route and instead define specific routes using ProfileXML as required.

Additional Information

Always On VPN Client DNS Server Configuration

Deploying Windows 10 Always On VPN with Microsoft Intune

Windows 10 Always On VPN Certificate Requirements for IKEv2

Windows 10 Always On VPN Certificate Requirements for SSTP

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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