Always On VPN and Entra Conditional Access

Microsoft recently introduced Entra Private Access, an identity-centric Zero Trust Network Access (ZTNA) solution to provide secure remote access to on-premises resources. With Entra Private Access, administrators can leverage Entra Conditional Access to enforce policy-based access control for network access. However, Entra Private Access isn’t for everyone. It does not provide full feature parity with Always On VPN, and there are also licensing considerations. However, for those organizations using Always On VPN, the good news is that you can integrate Entra Conditional Access with Always On VPN today to gain some of the security benefits it provides.

Conditional Access

Microsoft Entra Conditional Access is a security feature that enables administrators to create and enforce policies that specify how users can access resources. In the specific case of Always On VPN, conditional access is critical to ensuring legitimate access to authenticated users on authorized devices.

Signals

Conditional access policies use a wide variety of signals for policy enforcement, such as:

  • User Identity: Who is making this access request?
  • User Properties: Is this user a member of a specific group?
  • Location: Where is this access request originating?
  • Device Management: Is this device joined to Entra ID?
  • Device State: Is this device compliant with security policies?
  • Device Platform: Is this a Windows device?
  • Risk Level: Is this login considered risky?

Access Control

Based on these signals, administrators can design a conditional access policy to enforce granular access control, such as:

  • Grant access only from managed devices
  • Deny access from untrusted locations
  • Require additional context-based authentication (e.g., multifactor authentication)
  • Enforce specific authentication types (e.g., phishing-resistant credentials)
  • Allow access only from specific device platforms (e.g., Windows only)
  • Require Entra hybrid-joined device
  • Block access when a device is not compliant with security policies

Always On VPN

Entra Conditional Access works with Always On VPN by issuing a special, short-lived user authentication certificate once the user has been authorized. The Always On VPN infrastructure can be configured to use this certificate to grant access to the VPN. Integrating conditional access with Always On VPN can significantly improve the security posture of organizations using this feature.

Deployment Guide

I’ve published a detailed, step-by-step deployment guide to configure Entra conditional access for Always On VPN. In addition, I have posted a demonstration video for enabling Entra conditional access with Aways On VPN on YouTube.

Additional Information

Microsoft Entra Conditional Access Overview

Configure Entra Conditional Access for Always On VPN

Always On VPN Ask Me Anything (AMA) January 2025

It’s that time again! I realize it’s been a while since we’ve had one of these events. However, it’s a new year and we’re planning to get together again on Tuesday, January 21, 2025, at 10:00 AM PST (UTC-7).

Do you have questions about Always On VPN? Are you having a specific issue you can’t figure out? Would you like more information about configuration options? Here’s your chance to get your questions answered! Register now and join the session for an opportunity to ask me anything (AMA!) about Microsoft Windows Always On VPN and related technologies.

The AMA will be an open forum session where we can all talk shop about Always On VPN. It’s a great chance to learn new things and share experiences with your peers. We’ll discuss known issues and limitations, best practices, and more. I’m planning to have some special guests as well, so be sure to join us!

Everyone is welcome. Don’t miss out on this excellent opportunity to connect and learn. Register now!

Can’t make the session? Register anyway, and I’ll send you the link to the recording as soon as it is available!

Migrating from Always On VPN DPC Commercial to Open Source

Always On VPN Dynamic Profile Configurator (DPC) is a software solution that enables administrators to deploy and manage Always On VPN client configuration settings using Active Directory and Group Policy or Microsoft Intune. DPC began life as a commercial product. Recently, DPC has been released to the public via open source. DPC open source allows administrators everywhere to deploy the solution without cost. If you’re not using DPC today, I’d strongly recommend it. If you were previously a DPC commercial customer, you’ll want to migrate to DPC open source soon.

We’re on Discord! Join the conversation: https://discord.aovpndpc.com/.

Migration

Migrating from DPC commercial to open source requires the administrator to deploy a Group Policy Object (GPO) and client software in a specific order to avoid disruption to end users. Perform the following steps to complete the migration.

GPO Files

Download the DPC v5.0 (open source) group policy settings file (ADMX) file here and the language definition (ADML) file here.

After downloading the files, copy dpc.admx to the following location.

\\<DC name>\sysvol\<domain name>\Policies\PolicyDefinitions

Next, copy dpc.adml to the following location.

\\<DC name>\sysvol\<domain name>\Policies\PolicyDefinitions\en-US

Once complete, allow domain controller replication to finish before deploying DPC group policy settings.

New GPO

Create a new GPO that will contain the VPN client configuration settings. Do NOT copy the original DPC commercial GPO. Starting with a blank GPO is best to ensure proper operation and prevent conflicts. Also, please note the location for DPC settings has changed. The new location for DPC v5.0 settings is:

Computer Configuration > Policies > Administrative Templates > DPC Client

You can now link the GPO to the applicable OU(s) or complete this task before deploying the new software.

Migration Tool

The easiest way to migrate from DPC commercial to open source is to migrate the settings from the current GPO to a new one. A PowerShell script is available to simplify this task. You can download the Migrate-DpcConfig.ps1 PowerShell script here.

Note: It is not strictly required to migrate your current settings from DPC commercial. Although this migration script makes importing settings easier, nothing prevents you from creating a new GPO for DPC open source and starting from scratch if you wish.

Prerequisites

The PowerShell migration script requires the installation of the Remote Server Administration Tools (RSAT). Specifically, the Group Policy Management tools are needed. Although it’s possible to run this script on a domain controller, it is not recommended. The best practice is to install the RSAT tools on an administrative workstation or server.

You can install the necessary RSAT feature on Windows 11 by opening an elevated PowerShell or command window and running the following command.

dism.exe /Online /add-capability /CapabilityName:Rsat.GroupPolicy.Management.Tools~~~~0.0.1.0

On Windows Server, you can install the Group Policy Management tools by opening an elevated PowerShell command window and running the following command.

Install-WindowsFeature -Name GPMC

Once complete, restart the server to complete the installation process.

Import Settings

To migrate the DPC settings, open an elevated PowerShell command window and run the following command.

.\Migrate-DpcSetting.ps1 -PreviousGPOName <name of old DPC GPO> -NewGPOName <name of new DPC GPO>

For example,

.\Migrate-DpcSetting.ps1 -PreviousGPOName ‘Always On VPN DPC’ -NewGPOName ‘Always On VPN DPC – Open Source’

Apply GPO

If not done earlier, link the new DPC open-source GPO to the applicable OU(s). Do NOT unlink or delete the old GPO until all endpoints have been upgraded to the DPC v5.0 client.

Install Software

Once the new GPO has been configured and applied in Active Directory, the next step is to upgrade the DPC commercial client to the DPC open source client (v5.0). Software can be deployed via GPO using Active Directory software installation, SCCM, or any other method you use in your environment to deploy software. No switches or additional parameters are required to perform the upgrade. Simply run the .MSI file on the device, and the upgrade will occur automatically.

Important Note: Administrators must ensure that the new GPO settings are applied to the endpoint before installing the DPC v5.0 client.

Clean Up

After all endpoints have been upgraded to DPC v5.0, administrators can remove the DPC commercial GPO from AD. In addition, the commercial DPC ADMX and ADML files can be removed from domain controllers if desired.

Need Help?

If you’d like assistance migrating DPC commercial to open source, please don’t hesitate to reach out! I’m available to answer questions or provide remote assistance if necessary. You can reach me on the DPC-Chat channel on Discord here. Alternatively, you can fill out the form below, and I’ll provide more information.

Additional Information

PowerON Platforms Are No More

Always On VPN DPC Open Source

Always On VPN DPC Advanced Features

Always On VPN DPC with Microsoft Intune