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 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

Always On VPN Certificate Requirements for IKEv2

Always On VPN Certificate Requirements for IKEv2Internet Key Exchange version 2 (IKEv2) is one of the VPN protocols supported for Windows 10 Always On VPN deployments. When the VPN server is Windows Server 2016 with the Routing and Remote Access Service (RRAS) role configured, a computer certificate must first be installed on the server to support IKEv2. There are some unique requirements for this certificate, specifically regarding the subject name and Enhanced Key Usage (EKU) configuration. In addition, some deployment scenarios may require a certificate to be provisioned to the client to support IKEv2 VPN connections.

Server Certificate

The IKEv2 certificate on the VPN server must be issued by the organization’s internal private certification authority (CA). It must be installed in the Local Computer/Personal certificate store on the VPN server. The subject name on the certificate must match the public hostname used by VPN clients to connect to the server, not the server’s hostname. For example, if the VPN server’s hostname is VPN1 and the public FQDN is vpn.example.net, the subject field of the certificate must include vpn.example.net, as shown here.

Always On VPN Certificate Requirements for IKEv2

In addition, the certificate must include the Server Authentication EKU (1.3.6.1.5.5.7.3.1). Optionally, but recommended, the certificate should also include the IP security IKE intermediate EKU (1.3.6.1.5.5.8.2.2).

Always On VPN Certificate Requirements for IKEv2

Client Certificate

Client certificate requirements vary depending on the type of VPN tunnel and authentication method being used.

User Tunnel

No certificates are required on the client to support IKEv2 when using MSCHAPv2, EAP-MSCHAPv2, or Protected EAP (PEAP) with MSCHAPv2. However, if the option to verify the server’s identity by validating the certificate is selected when using PEAP, the client must have the certificates for the root CA and any subordinate CAs installed in its Trusted Root Certification and Intermediate Certificate Authorities certificate stores, respectively.

User Tunnel with Certificate Authentication

Using certificate authentication for the user tunnel is the recommended best practice for Always On VPN deployments. A client certificate must be installed in the Current User/Personal store to support PEAP authentication with smart card or certificate authentication. The certificate must include the Client Authentication EKU (1.3.6.1.5.5.7.3.2).

Always On VPN Certificate Requirements for IKEv2

Device Tunnel

A computer certificate must be installed in the Local Computer/Personal certificate store to support IKEv2 machine certificate authentication and the Always On VPN device tunnel. The certificate must include the Client Authentication EKU (1.3.6.1.5.5.7.3.2).

Always On VPN Certificate Requirements for IKEv2

More information about configuring the Always On VPN device tunnel can be found here.

Additional Information

Always On VPN with Trusted Platform Module (TPM) Certificates

Always On VPN Protocol Recommendations for Windows Server 2016 RRAS

Always On VPN and Windows Server RRAS

Always On VPN Training

DirectAccess and Always On VPN with Trusted Platform Module (TPM) Certificates

DirectAccess and Always On VPN with Trusted Platform Module (TPM) CertificatesTo enhance security when provisioning certificates for DirectAccess (computer) or Windows 10 Always On VPN (user) it is recommended that private keys be stored on a Trusted Platform Module (TPM) on the client device. A TPM is a dedicated security processor included in nearly all modern computers. It provides essential hardware protection to ensure the highest levels of integrity for digital certificates and is used to generate, store, and restrict the use of cryptographic keys. It also includes advanced security and protection features such as key isolation, non-exportability, and anti-hammering to prevent brute-force attacks.

To ensure that private keys are created and stored on a TPM, the certificate template must be configured to use the Microsoft Platform Crypto Provider. Follow the steps below to configure a certificate template required to use a TPM.

  1. Open the Certificate Templates management console (certtmpl.msc) and duplicate an existing certificate template. For example, if creating a certificate for DirectAccess, duplicate the Workstation Authentication certificate template. For Always On VPN, duplicate the User certificate template.
  2. On the Compatibility tab, ensure the Certification Authority and Certificate recipient compatibility settings are set to a minimum of Windows Server 2008 and Windows Vista/Server 2008, respectively.DirectAccess and Always On VPN with Trusted Platform Module (TPM) Certificates
  3. Select the Cryptography tab.
  4. Choose Key Storage Provider from the Provider Category drop down list.
  5. Choose the option Requests must use one of the following providers and select Microsoft Platform Crypto Provider.DirectAccess and Always On VPN with Trusted Platform Module (TPM) Certificates

Note: If Microsoft Platform Crypto Provider does not appear in the list above, got to the Request Handling tab and uncheck the option Allow private key to be exported.

Complete the remaining certificate configuration tasks (template display name, subject name, security settings, etc.) and publish the certificate template. Client machines configured to use this template will now have a certificate with private key fully protected by the TPM.

Additional Resources

Trusted Platform Module (TPM) Fundamentals

DirectAccess and Always On VPN Certificate Auto Enrollment

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

 

NetMotion Mobility Device Tunnel Configuration

NetMotion Mobility Device Tunnel ConfigurationIn its default configuration, NetMotion Mobility connections are established at the user level. In most cases this level of access is sufficient, but there are some common uses cases that require VPN connectivity before the user logs on. Examples include provisioning a new device to a user who has never logged on before, or to allow support engineers to connect to a remote device without requiring a user to log in first.

Infrastructure Requirements

To support NetMotion Mobility’s “unattended mode” (device tunnel) it will be necessary to deploy a Windows Server 2016 (or 2012R2) Network Policy Server (NPS). In addition, an internal private certification authority (CA) will be required to issue certificates to the NPS server and all NetMotion Mobility client computers.

Client Certificate Requirements

A certificate with the Client Authentication Enhanced Key Usage (EKU) must be provisioned to the local computer certificate store on all NetMotion Mobility clients that require a device tunnel (figure 1). The subject name on the certificate must match the fully qualified domain name of the client computer (figure 2). It is recommended that certificate auto enrollment be used to streamline the provisioning process.

NetMotion Mobility Device Tunnel Configuration

Figure 1. Computer certificate with Client Authentication EKU.

NetMotion Mobility Device Tunnel Configuration

Figure 2. Computer certificate with subject name matching the client computer’s hostname.

NPS Server Certificate Requirements

A certificate with the Server Authentication EKU must be provisioned to the local computer certificate store on the NPS server (figure 3). The subject name on the certificate must match the fully qualified domain name of the NPS server (figure 4).

NetMotion Mobility Device Tunnel Configuration

Figure 3. Computer certificate with Server Authentication EKU.

NetMotion Mobility Device Tunnel Configuration

Figure 4. Computer certificate with subject name matching the NPS server’s hostname.

NPS Server Configuration

Next install the NPS server role by running the following PowerShell command.

Install-WindowsFeature NPAS -IncludeMamagementTools

Once complete, open the NPS server management console and perform the following steps.

Note: Below is a highly simplified NPS configuration designed for a single use case. It is provided for demonstration purposes only. The NPS server may be used by more than one network access server (NAS) so the example policies included below may not work in every deployment.

  1. Expand RADIUS Clients and Servers.
  2. Right-click RADIUS clients and choose New.
  3. Select the option to Enable this RADIUS client.
  4. Enter a friendly name.
  5. Enter the IP address or hostname of the NetMotion gateway server.
  6. Click Verify to validate the hostname or IP address.
  7. Select Manual to enter a shared secret, or select Generate to create one automatically.
  8. Copy the shared secret as it will be required when configure the NetMotion Mobility gateway server later.
  9. Click OK.
    NetMotion Mobility Device Tunnel Configuration
  10. Expand Policies.
  11. Right-click Network Policies and choose New.
  12. Enter a descriptive name for the new policy.
  13. Select Type of network access server and choose Unspecified.
  14. Click Next.
    NetMotion Mobility Device Tunnel Configuration
  15. Click Add.
  16. Select Client IPv4 Address.
  17. Click Add.
  18. Enter the internal IPv4 address of the NetMotion Mobility gateway server.
  19. Click OK.
  20. Click Next.
    NetMotion Mobility Device Tunnel Configuration
  21. Select Access granted.
  22. Click Next.
    NetMotion Mobility Device Tunnel Configuration
  23. Click Add.
  24. Choose Microsoft: Protected EAP (PEAP).
  25. Click OK.
  26. Select Microsoft: Protected EAP (PEAP).
  27. Click Edit.
  28. Choose the appropriate certificate in the Certificate issued to drop down list.
  29. Select Secure password (EAP-MSCHAP v2).
  30. Click Remove.
  31. Click Add.
  32. Choose Smart Card or other certificate.
  33. Click OK.
  34. Select Smart Card or other certificate.
  35. Click Edit.
  36. Choose the appropriate certificate in the Certificate issued to drop down list.
  37. Click OK.
    NetMotion Mobility Device Tunnel Configuration
  38. Uncheck all options beneath Less secure authentication methods.
  39. Click Next three times.
  40. Click Finish.
    NetMotion Mobility Device Tunnel Configuration

Mobility Server Configuration

Open the NetMotion Mobility management console and perform the following steps.

  1. In the drop-down menu click Configure.
  2. Click Authentication Settings.
  3. Click New.
  4. Enter a descriptive name for the new authentication profile.
  5. Click OK.
  6. Expand Authentication.
  7. Select Mode.
  8. Select Unattended Mode Authentication Setting Override.
  9. From the Authentication mode drop-down box choose Unattended.
  10. Click Apply.
    NetMotion Mobility Device Tunnel Configuration
  11. Expand RADIUS: Device Authentication.
  12. Select Servers.
  13. Select [Profile Name] Authentication Setting Override.
  14. Click Add.
  15. Enter the IP address of the NPS server.
  16. Enter the port (default is 1812).
  17. Enter the shared secret.
  18. Click OK.
    NetMotion Mobility Device Tunnel Configuration
  19. In the drop-down menu click Configure.
  20. Click Client Settings.
  21. Expand Device Settings.
  22. Select the device group to enable unattended mode for.
  23. Expand Authentication.
  24. Select Settings Profile.
  25. Select [Device Group Name] Group Settings Override.
  26. In the Profile drop-down menu choose the authentication profile created previously.
  27. Click Apply.
    NetMotion Mobility Device Tunnel Configuration

Validation Testing

If everything is configured correctly, the NetMotion Mobility client will now indicate that the user and the device have been authenticated.

NetMotion Mobility Device Tunnel Configuration

Summary

Enabling unattended mode with NetMotion Mobility provides feature parity with DirectAccess machine tunnel and Windows 10 Always On VPN device tunnel. It ensures that domain connectivity is available before the user logs on. This allows users to log on remotely without cached credentials. It also allows administrators to continue working seamlessly on a remote computer after a reboot without having a user present to log on.

Additional Resources

NetMotion Mobility as an Alternative to DirectAccess

 

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShellWindows 10 Always On VPN and DirectAccess both provide seamless, transparent, always on remote network access for Windows clients. However, Always On VPN is provisioned to the user, not the machine as it is with DirectAccess. This presents a challenge for deployment scenarios that require the VPN connection to be established before the user logs on. To address this issue, Microsoft introduced support for a device tunnel configuration option beginning with Windows 10 version 1709 (Fall creators update).

Want to learn more about Windows 10 Always On VPN? Register for one of my hands-on training classes now forming in cities across the U.S. Details here.

Prerequisites

To support an Always On VPN device tunnel, the client computer must be running Windows 10 Enterprise or Education version 1709 (Fall creators update). It must also be domain-joined and have a computer certificate with the Client Authentication Enhanced Key Usage (EKU) issued by the organization’s Public Key Infrastructure (PKI).

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

In addition, only the built-in Windows VPN client is supported for Always On VPN device tunnel. Although Windows 10 Always On VPN user connections can be configured using various third-party VPN clients, they are not supported for use with the device tunnel.

VPN ProfileXML

The Always On VPN device tunnel is provisioned using an XML file. You can download a sample VPN ProfileXML file here. Make any changes required for your environment such as VPN server hostnames, routes, traffic filters, and remote address ranges. Optionally include the trusted network detection code, if required. Do not change the protocol type or authentication methods, as these are required.

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Reference: https://docs.microsoft.com/en-us/windows-server/remote/remote-access/vpn/vpn-device-tunnel-config#configure-the-vpn-device-tunnel

Once the ProfileXML file is created, it can be deployed using Intune, System Center Configuration Manager (SCCM), or PowerShell. In this post I’ll cover how to configure Windows 10 Always On VPN device tunnel using PowerShell.

Client Configuration

Download the PowerShell script located here and then copy it to the target client computer. The Always On VPN device tunnel must be configured in the context of the local system account. To accomplish this, it will be necessary to use PsExec, one of the PsTools included in the Sysinternals suite of utilities. Download PsExec here, copy it to the target machine, and then run the following command in an elevated PowerShell command window.

PsExec.exe -i -s C:\windows\system32\WindowsPowerShell\v1.0\powershell.exe

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Another elevated PowerShell window will open, this one now running in the context of the local system account. In this window, navigate to the folder where you copied the PowerShell script and XML file to. Run the PowerShell script and specify the name of the ProfileXML file, as shown below.

VPN_Profile_Device.ps1 -xmlFilePath .\profileXML_device.XML -ProfileName DeviceTunnel

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

To verify creation of the VPN device tunnel, run the following PowerShell command.

Get-VpnConnection -AllUserConnection

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Note: Be advised that the ConnectionStatus is always Disconnected. Hopefully this will be addressed by Microsoft in the near future.

Server Configuration

If you are using Windows Server 2012 R2 or Windows Server 2016 Routing and Remote Access Service (RRAS) as your VPN server, you must enable machine certificate authentication for VPN connections and define a root certification authority for which incoming VPN connections will be authenticated with. To do this, open an elevated PowerShell command and run the following commands.

$VPNRootCertAuthority = “Common Name of trusted root certification authority”
$RootCACert = (Get-ChildItem -Path cert:LocalMachine\root | Where-Object {$_.Subject -Like “*$VPNRootCertAuthority*” })
Set-VpnAuthProtocol -UserAuthProtocolAccepted Certificate, EAP -RootCertificateNameToAccept $RootCACert -PassThru

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Summary

Once the Always On VPN device tunnel is configured, the client computer will automatically establish the connection as soon as an active Internet connection is detected. This will enable remote logins for users without cached credentials, and allow administrators to remotely manage Always On VPN clients without requiring a user to be logged on at the time.

Additional Information

Configure Windows 10 VPN Device Tunnel on Microsoft.com

3 Important Advantages of Always On VPN over DirectAccess

5 Things DirectAccess Administrators Should Know About Always On VPN 

Windows 10 Always On VPN and the Future of DirectAccess

Windows 10 Always On VPN Training and Consulting Services

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

Top 5 DirectAccess Troubleshooting Tips

Top 5 DirectAccess Troubleshooting TipsDirectAccess is a thing of beauty when everything is working as it should. When it isn’t, troubleshooting can be quite challenging. DirectAccess relies on many Windows platform technologies such as Active Directory for authentication, PKI for certificate management, group policy for settings deployment, IPsec for encryption, and IPv6 for transport. With so many dependencies, locating the source of the problem can be a difficult and daunting task.

I’m frequently called upon to help organizations of all sizes with DirectAccess troubleshooting. While this post is not intended to be a detailed, prescriptive guide for DirectAccess troubleshooting, I did want to share some common troubleshooting tips based on many years of troubleshooting DirectAccess.

Here are my top 5 DirectAccess troubleshooting tips:

  1. Check Prerequisites – Before diving in and collecting network traces and scouring event logs for clues as to why DirectAccess isn’t working, it’s essential to start at the beginning. Often the source of trouble is missing or misconfigured prerequisites. For example, is the DirectAccess client running a supported operating system? Remember, clients must be running Windows 10 Enterprise or Education, Windows 8.x Enterprise, or Windows 7 Enterprise or Ultimate. Also, ensure that the Windows firewall is enabled on DirectAccess servers and clients, that certificates are installed and valid (trusted, correct EKU, etc.), and that the DirectAccess settings GPO has been applied to servers and clients.
  2. Validate External Connectivity – If you are following implementation and security best practices for DirectAccess, the DirectAccess server will be in a perimeter/DMZ network behind an edge firewall. The firewall must be configured to allow inbound TCP port 443 only. If the firewall is also performing Network Address Translation (NAT), the NAT rule must be configured to forward traffic to the DirectAccess server’s dedicated or virtual IP address (VIP), or the VIP of the load balancer. Watch for routing issues when using load balancers too. It’s a good idea to confirm external connectivity using the Test-NetConnection PowerShell command. Even better, use the open source tool Nmap for more thorough testing.
  3. Remove Third Party Software – I can’t tell you how many times I’ve resolved DirectAccess connectivity issues by removing (not just disabling!) third party software on the client and/or server. It’s not uncommon for third-party security software to interfere with IPsec and/or IPv6 communication, both of which are vital to DirectAccess. If your DirectAccess troubleshooting efforts reveal no underlying issues with prerequisites or external connectivity, I’d suggest removing (at least temporarily) any third-party software and testing again.
  4. Isolate Environmental Issues – Occasionally other settings applied manually or via Active Directory group policy will interfere with DirectAccess. Examples include IPv6 being disabled in the registry, IPv6 transition technologies required to support DirectAccess are turned off, essential firewall rules for DirectAccess are disabled, or manipulating local security settings such as Access this computer from the network. To assist with troubleshooting it might be necessary to temporarily place DirectAccess clients and servers in their own dedicated Organizational Units (OUs) and block inheritance to isolate the configuration as much as possible. In addition, if DirectAccess clients are servers are provisioned using images or templates, testing with a clean build straight from the installation source (ISO or DVD) can be helpful.
  5. Check for Unsupported Configurations – If DirectAccess isn’t working, it might be possible the configuration you are trying to use is not supported. Examples including strong user authentication with OTP when force tunneling is enabled, provisioning Windows 7 clients when using Kerberos Proxy authentication, or provisioning Windows 10 clients when Network Access Protection (NAP) integration is enabled. These configurations won’t work and are formally documented here.

This is by no means a comprehensive or exhaustive troubleshooting guide. For more information and additional DirectAccess troubleshooting guidance I would encourage you to purchase my book Implementing DirectAccess with Windows Server 2016, which has an entire chapter devoted just to troubleshooting. In addition, watch my DirectAccess video training courses on Pluralsight for details and information about DirectAccess installation, configuration, management, support, and troubleshooting. And if you’re still struggling to resolve a DirectAccess problem, use the form at the bottom of this page to contact me to inquire about additional troubleshooting help.

Additional Resources

Microsoft Windows DirectAccess Client Troubleshooting Tool
DirectAccess and Windows 10 Professional
DirectAccess Troubleshooting with Nmap
DirectAccess Unsupported Configurations
Planning and Implementing DirectAccess with Windows Server 2016 Video Training Course on Pluralsight
Implementing DirectAccess with Windows Server 2016 Book

Need assistance with DirectAccess troubleshooting? Complete the form below and I’ll get in touch with you.

Planning and Implementing DirectAccess with Windows Server 2016 Video Training Course on Pluralsight

Planning and Implementing DirectAccess with Windows Server 2016I’m excited to announce my latest video training course, Planning and Implementing DirectAccess with Windows Server 2016, is now available on Pluralsight! In this course, I’ll provide a high-level overview of DirectAccess, compare it with VPN, and outline supporting infrastructure requirements. In addition, you’ll learn how to choose the best network topology for a DirectAccess deployment, how to prepare Active Directory and Public Key Infrastructure (PKI) for DirectAccess, and how to install and configure DirectAccess in Windows Server 2016 using the latest implementation and security best practices. You’ll also learn how to provision Windows 10 clients and understand the unique requirements for supporting Windows 7.

The course includes the following training modules:

Overview of DirectAccess
Planning for DirectAccess
Configuring DirectAccess with the Getting Started Wizard
Configuring DirectAccess with the Remote Access Setup Wizard
Provisioning DirectAccess Clients
Supporting Windows 7 Clients

Throughout the course, I share valuable knowledge and insight gained from more than 5 years of experience deploying DirectAccess for some of the largest organizations in the world. Pluralsight offers a free trial subscription if you don’t already have one, so watch my DirectAccess video training course today!

Additional Resources

Planning and Implementing DirectAccess with Windows Server 2016 on Pluralsight
Implementing DirectAccess with Windows Server 2016

Troubleshooting DirectAccess IP-HTTPS Error Code 0x800b0109

A Windows 7 or Windows 8.x/10 client may fail to establish a DirectAccess connection using the IP-HTTPS IPv6transition technology. When troubleshooting this issue, running ipconfig.exe show that the media state for the tunnel adapter iphttpsinterface is Media disconnected.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

Running the Get-NetIPHttpsState PowerShell command on Windows 8.x/10 clients or the netsh interface httpstunnel show interface command on Windows 7 clients returns an error code of 0x800b0109 with an interface status Failed to connect to the IPHTTPS server; waiting to reconnect.

Troubleshooting DirectAccess IP-HTTPS Error 0x80090326

Error code 0x800b0109 translates to CERT_E_UNTRUSTEDROOT, indicating the client was unable to establish an IP-HTTPS connection because the certificate presented during the SSL handshake was issued by a certification authority that was not trusted. This commonly occurs when the DirectAccess server is configured with an SSL certificate issued by the internal PKI and DirectAccess clients are provisioned using offline domain join without using the /rootcacerts switch. This can also happen if DirectAccess is configured to use a self-signed certificate for IP-HTTPS, and the certificate is either renewed or DirectAccess is uninstalled and reinstalled.

Troubleshooting DirectAccess IP-HTTPS Error 0x800b0109

To resolve IP-HTTPS error code 0x800b0109, obtain the root certificate for the certificate authority that issued the SSL certificate used for IP-HTTPS and import it in to the DirectAccess client’s Trusted Root Certification Authorities local computer certificate store. Once complete, restart the IP helper service to reinitiate an IP-HTTPS connection.

Additional Information

Provisioning DirectAccess Clients using Windows Offline Domain Join

Troubleshooting DirectAccess IP-HTTPS Error Code 0x90320

Troubleshooting DirectAccess IP-HTTPS Error 0x2af9

DirectAccess Expired IP-HTTPS Certificate and Error 0x800b0101

SSL Certificate Considerations for DirectAccess IP-HTTPS

Implementing DirectAccess with Windows Server 2016

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