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

Microsoft Ignite 2024

The Microsoft Ignite conference will be held November 19-22, 2024, at the McCormick Place Conference Center in Chicago, IL. Ignite is the premier Microsoft event of the year and will be packed with many announcements about new products and technologies. Ignite is also a fantastic learning event with experts worldwide in attendance.

Meet Up

I’m excited to announce that Microsoft has invited me to participate in the event as part of their Expert Meet-Up program. I will spend time at the Windows Server station in the Azure Infrastructure section of the Hub. Below are the days and times I’ll be available.

  • Tuesday, November 19 – 3:30 PM to 7:30 PM CST
  • Wednesday, November 20 – 2:30 PM to 6:00 PM CST
  • Thursday, November 21 – 2:30 PM to 6:00 PM CST

Let’s Connect

Be sure to drop by and say hello! We can chat about Windows Server and Azure Infrastructure. Of course, we can also discuss all the technologies I usually work with, including Entra Private Access, Always On VPN, Intune and Cloud PKI, and certificates in general. I will also attend many social gatherings during the week, so look for me at those as well.

I look forward to seeing you at the event!

Additional Information

Microsoft Ignite 2024