Always On VPN Proxy Server Configuration

Always On VPN Proxy Server Configuration

Web proxy servers are not as common today as they once were, but a few organizations still leverage them to provide secure Internet access for their employees. Commonly they are used to inspect and control Internet traffic and to enforce acceptable use policies. Some organizations may wish to extend this protection to Always On VPN clients in the field by enabling force tunneling. Administrators can define a web proxy server for Always On VPN connections globally for web traffic or individual websites or domains.

VPN Proxy

A VPN web proxy server can be defined when the Always On VPN user tunnel connection uses force tunneling. Although you can still configure a VPN web proxy server with split tunneling enabled, it will not work. It is only functional when force tunneling is in use.

Administrators can configure a VPN web proxy server using the Microsoft Endpoint Manager UI or custom XML deployed with Endpoint Manager or PowerShell. Administrators can define a VPN web proxy server explicitly, or a proxy automatic configuration (PAC) file can be specified.

Note: VPN proxy server settings only work when force tunneling is enabled. Force tunneling is an unsupported configuration for the device tunnel, making the global proxy server setting for the device tunnel unsupported.

Proxy Autoconfiguration

Perform the following steps to configure a VPN web proxy server with a PAC file in Endpoint Manager.

  1. Expand the Proxy section in the Configuration settings of the Always On VPN configuration profile.
  2. Enter the URL for the PAC file in the Automatic configuration script field. Be sure to include the port number in the URL when using a non-standard port.
  3. Leave the Address and Port number fields blank.
  4. Choose Enable or Disable from the Bypass proxy for local addresses drop-down list.

To configure a VPN web proxy server with a PAC file using custom XML, include the following code between the <VPNProfile> and </VPNProfile> tags in the Always On VPN XML configuration file.

Explicit Proxy

Perform the following steps to configure an explicit VPN web proxy server in Endpoint Manager.

  1. Enter the IP address, hostname, or fully qualified domain name (recommended) in the Address field.
  2. Enter the port number in the Port number field.
  3. Choose Enable or Disable from the Bypass proxy for local addresses drop-down list.

To configure an explicit VPN web proxy server using custom XML, include the following code between the <VPNProfile> and </VPNProfile> tags in the Always On VPN XML configuration file.

Namespace Proxy

Administrators can also define VPN web proxy servers on a per-namespace or per-hostname basis. Namespace VPN proxy servers can be helpful for scenarios where routing public websites over the Always On VPN connection is required. Most commonly, this is necessary because the public website restricts access to the IP address of the on-premises Internet gateway.

A namespace VPN proxy server is implemented using a Name Resolution Policy Table (NRPT) rule. At the time of this writing, a bug in Microsoft Endpoint Manager prevents administrators from deploying this option using the UI.

As you can see here, administrators can specify a proxy server as part of an NRPT rule in the Endpoint Manager UI. Notice this section of the UI validates the proxy FQDN correctly.

Always On VPN Proxy Server Configuration

However, when you try to save the configuration profile, Endpoint Manager returns the following error.

“Unable to save due to invalid data. Update your data then try again: ProxyServerUri must be a valid URL or be empty.”

Interestingly, when entering a URL such as http://proxy.lab.richardhicks.net:8080/ in the Proxy field, the Endpoint Manager UI accepts it and successfully validates. But according to the VPNv2 Configuration Service Provider (CSP) reference, the value must be entered as an IP address. A hostname or FQDN also works based on my testing. Entering a URL as shown in the example above will not work at all.

With that, the only way to implement a namespace VPN web proxy server is to use custom XML. To do this, include the following code between the <VPNProfile> and </VPNProfile> tags in the Always On VPN XML configuration file.

Include the leading “.” to specify the entire domain, as shown above. Omit the leading “.” to specify an individual host (for example, app.richardhicks.com). Repeat this section for each additional host or domain, as required.

Caveat

Unfortunately, the Microsoft Internet Explorer web browser is the only browser that functions with the namespace VPN web proxy server. All modern web browsers, including Microsoft Edge, ignore the namespace proxy setting entirely, which seriously limits this feature’s usefulness in most organizations today.

Workaround

If routing a public website over the Always On VPN tunnel is required, adding its IP address(es) to the Always On VPN connection’s routing table is needed. However, doing this presents some unique challenges, as public websites frequently have many IP addresses, which are often dynamically changing. Also, it is common for public websites to pull content from many different domains or use Content Delivery Networks (CDNs), making the problem of identifying which IP addresses to add to the Always On VPN connection’s routing table even more challenging. Further, administrators must update the client configuration each a public website’s IP address changes, adding significant management overhead.

Summary

Routing client Internet traffic through an on-premises web proxy server for Always On VPN clients works well when force tunneling is enabled. Administrators can explicitly define a web proxy server or use a proxy automatic configuration (PAC) file. All web browsers work without issue in this scenario. Using a namespace proxy is only effective when browsing with Microsoft Internet Explorer. All modern web browsers, including Microsoft Edge, ignore namespace proxy settings.

Additional Information

Windows 10 Always On VPN and the Name Resolution Policy Table (NRPT)

Windows 10 VPNv2 Configuration Service Provider (CSP) Reference

Windows 10 Always On VPN Client DNS Server Configuration

Always On VPN and Autopilot Hybrid Azure AD Join

Always On VPN and Autopilot Hybrid Azure AD Join

Windows Autopilot is a cloud-based technology that administrators can use to configure new devices wherever they may be, whether on-premises or in the field. Devices provisioned with Autopilot are Azure AD joined by default and managed using Microsoft Endpoint Manager. Optionally, an administrator can enable hybrid Azure AD join by also joining the device to an on-premises Active Directory domain using a domain join configuration profile in conjunction with the offline domain-join connector. Although enabling hybrid Azure AD join might sound appealing, there are specific deployment scenarios that present some rather unique and challenging problems when using this option.

Offline Hybrid Azure AD Join

For field-based devices, the device must have connectivity to a domain controller to support the initial login when the user has no local cached credentials. The Always On VPN device tunnel can be deployed in this scenario to provide connectivity and allow the user to log in to a new device the first time without being on-premises. The Always On VPN device tunnel is easily deployed using a Microsoft Endpoint Manager configuration profile. Certificates required to support the device tunnel can be deployed with Microsoft Endpoint Manager and one of the certificate connectors for Microsoft Endpoint Manager.

Windows 10 Professional

If a Windows 10 Professional device is configured using Autopilot, and hybrid Azure AD joined is enabled, the Always On VPN device tunnel can still be provisioned, but it won’t start automatically because it requires Enterprise Edition to be fully functional. This prevents the user from being able to logon the first time. The device must be upgraded to Enterprise Edition before the first user logon. There are multiple ways to accomplish this depending on the deployment scenario and activation requirements.

Multiple Activation Key

The easiest way to upgrade Windows 10 Professional to Enterprise Edition is to obtain a Multiple Activation Key (MAK) and deploy that to clients using a Microsoft Endpoint Manager configuration profile. Follow the steps below to create a configuration profile to perform this upgrade.

  1. Open the Microsoft Endpoint Manager console and click on Devices > Configuration Profiles.
  2. Click Create profile.
  3. Select Windows 10 and later in the Platform drop-down list.
  4. Select Templates in the Profile type drop-down list.
  5. Select Edition upgrade and mode switch from the list of templates.
  6. Click Create.

Use the following steps to configure the settings for the configuration profile.

  1. Enter a descriptive name for the configuration profile in the Name field.
  2. Enter a description for the profile in the Description field (optional).
  3. Click Next.
  4. Expand the Edition Upgrade section and select Windows 10 Enterprise from the Edition to upgrade to drop-down list.
  5. Enter your multiple activation product key in the Product Key field.

    Always On VPN and Autopilot Hybrid Azure AD Join

Once complete, assign the configuration profile to the appropriate groups and click Create.

KMS Activation

If Key Management Service (KMS) activation is required, follow the steps listed previously for MAK. Enter the KMS client setup key for Windows 10 Enterprise which is NPPR9-FWDCX-D2C8J-H872K-2YT43. The device will complete KMS activation when it can connect to the on-premises KMS host.

Subscription Activation

Windows 10 Enterprise Edition licensing is included in some Microsoft 365 subscriptions. This poses a unique challenge for hybrid Azure AD join scenarios, however. Specifically, subscription activation is a “step-up” process that requires Windows 10 Professional to have been successfully activated previously. Also, this occurs after the user logs on, but the user cannot log on unless the device tunnel is active. Catch 22!

Workaround

A multi-step process is required to address the limitations imposed by subscription activation. To begin, the device must be upgraded to Enterprise Edition, so the device tunnel is available for the initial user logon. This is a temporary, one-time upgrade to Enterprise Edition solely for the purpose of getting the device tunnel to connect and allow the user to authenticate.

To begin, download this PowerShell script and follow the steps below to deploy it to Windows 10 devices using Microsoft Endpoint Manager.

  1. Open the Microsoft Endpoint Manager console and click on Devices > Scripts.
  2. Click Add and select Windows 10.
  3. Enter a descriptive name for the configuration profile in the Name field.
  4. Enter a description for the profile in the Description field (optional).
  5. Click Next.
  6. Enter the location of the PowerShell script in the Script location field.
  7. Click Next, then assign the script to the appropriate device group(s) and click Add.

The PowerShell script will automatically install the KMS client setup key for Windows 10 Enterprise Edition, then restart the network interfaces to ensure the device tunnel starts. This will immediately upgrade the client device to Windows 10 Enterprise Edition and allow the user to authenticate.

Subscription activation with a step-up upgrade to Enterprise Edition still requires that Windows 10 Professional be activated first. To accomplish this, the embedded Windows 10 Professional key must be re-installed on the client. To do this, download this PowerShell script and follow the same steps listed previously to deploy a PowerShell script with Microsoft Endpoint Manager. However, this script should be assigned to users, not devices.

Once this script is run on the client it will be downgraded (temporarily) to Windows 10 Professional edition. After activation is successful, subscription activation will once again upgrade the client to Windows 10 Enterprise Edition.

Considerations

As you can see, the process of getting a Windows 10 Professional edition client onboarded in a hybrid Azure AD joined scenario is somewhat complex. My advice is to avoid this scenario whenever possible. Access to on-premises resources with the Always On VPN user tunnel with full single sign-on support is still available for users on Windows 10 devices that are Azure AD joined only. Unless there is a specific requirement to manage client devices using on-premises Active Directory and group policy, consider choosing native Azure AD join with Autopilot and manage devices using Microsoft Endpoint Manager exclusively.

Special Thanks

I would like to extend a special thank you to everyone in the Microsoft Endpoint Manager community who provided valuable input and feedback for me on this topic, especially John Marcum, Michael Niehaus, and Sandy Zeng. Follow the #MEMCM hashtag on Twitter to keep up on all things Microsoft Endpoint Manager.

Additional Information

Overview of Windows Autopilot

Windows 10 Subscription Activation

Windows 10 Always On VPN Class-Based Default Route and Microsoft Endpoint Manager

Windows 10 Always On VPN Device Tunnel and Custom Cryptography in Microsoft Endpoint Manager

Always On VPN Class-Based Default Route and Intune

`Always On VPN Class-Based Default Route and IntuneIn a recent post, I described how to configure routing for Windows 10 Always On VPN clients. In that article, I shared guidance for disabling the class-based default route in favor of defining specific routes for the VPN client. While this is easy enough to do when you use custom XML (deployed via PowerShell, SCCM, or Intune), there is a known limitation when using the native Intune UI that could present some challenges.

Intune VPN Profile Configuration

Defining specific routes is easy to do in Intune using the native VPN configuration profile. In the Configuration settings expand Split Tunneling and click Enable. The administrator can then add routes by entering their Destination prefix and Prefix size, as shown here.

Always On VPN Class-Based Default Route and Intune

Class-Based Default Route

The limitation with using Intune to configure routes is that there is currently no option to disable the class-based default route as there is with custom XML. This means the routes shown in the example above will be added to the client, but the class-based route will also be added automatically, as shown here (class-based default route highlighted with the arrow).

Always On VPN Class-Based Default Route and Intune

Considerations

In most cases, the inclusion of the class-based default route along with the administrator-defined routes will not be a problem. However, in some scenarios, it could yield unexpected results. Specifically, Always On VPN clients may have unintended access to some networks over the VPN tunnel. This is most significant for the Always On VPN device tunnel, where it is common to limit access to only specific resources using individual host routes.

Workaround

Today there is no option to disable the class-based default route using the native Intune UI. Your only option is to deploy the Always On VPN profile using custom XML, as described here.

Additional Information

Deploying Windows 10 Always On VPN with Intune and Custom XML

Deploying Windows 10 Always On VPN Device Tunnel with Intune and Custom XML

Windows 10 Always On VPN Routing Configuration

Windows 10 Always On VPN Device Tunnel Operation and Best Practices

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