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

Microsoft Security Service Edge Now Generally Available

A few weeks ago, Microsoft announced the general availability of its Security Service Edge (SSE) offering, Global Secure Access (GSA). GSA encompasses Entra Internet Access, a cloud-based Secure Web Gateway, and Entra Private Access, a Zero Trust Network Access (ZTNA) solution for accessing private data and applications on-premises.

ZTNA vs. VPN

Entra Private Access will be a compelling alternative to traditional VPN solutions such as Windows Always On VPN. Where traditional VPNs grant the endpoint an IP address on the internal network, Entra Private Access provides more granular access and does not require the device to be directly connected to the network.

GSA Client

Administrators must install the GSA client on all endpoints using Entra Internet Access or Entra Private Access. Today, the client is available for Windows and Android devices. iOS and macOS clients are forthcoming.

Private Network Connector

The Entra Private Access solution relies on the Entra Private Network Connector. The Entra Private Network Connector is a software component installed on-premises that provides remote access connectivity. Previously, it was called the Azure AD Application Proxy. Essentially, it is the same technology extended to support TCP and UDP network access in addition to HTTP.

Limitations

Entra Private Access is the way of the future for secure remote access. However, today, there are still some important limitations associated with this technology.

Private DNS

Although Microsoft announced general availability for Entra Private Access, it still lacks the private DNS feature many organizations require to provide feature parity with their existing VPN. This feature is still in private preview at the time of this writing. Hopefully, Microsoft will release this feature soon.

Device Connection

Entra Private Access does not support device-based connections. This limits its capabilities for domain-joined devices. If your organization uses hybrid Entra join today, consider sticking with Always On VPN until you move to native Entra joined endpoints.

Licensing

Global Secure Access (Entra Private Access and Entra Internet Access) are included in the Microsoft Entra Suite license. More information about Entra licensing can be found here.

Additional Information

Microsoft Global Secure Access Now Generally Available

Microsoft Entra Global Secure Access (GSA) Overview

Microsoft Entra Security Service Edge (SSE) on the RunAs Radio Podcast

Microsoft Entra Plans & Pricing