All posts in category Network Device Enrollment Services

Azure Conditional Access Certificates with SID Information Now Available

I recently wrote about changes to certificate-based authentication affecting Always On VPN implementations. These changes were introduced by Microsoft’s security update KB5014754. When the update is installed on domain controllers and enterprise Certification Authorities (CAs), administrators can perform strong user mapping for certificates used for Active Directory authentication. However, when first introduced, the update came with some serious limitations that prevented administrators from enabling full enforcement mode for certificate mapping.

Limitations

When KB5014754 is installed on an enterprise issuing CA, a new certificate extension (1.3.6.1.4.1.311.25.2) is added to the issued certificate that includes the principal’s (user or device) Security Identifier (SID). However, this only occurs when an online template is used. An online template is one with the subject name built from Active Directory information. The SID is not embedded in certificates issued using an offline template. Offline templates are templates where the subject name is supplied in the request. There are two scenarios where this causes problems for Always On VPN.

Microsoft Intune

Certificates delivered with Microsoft Intune via the Intune Certificate Connector use an offline template. This applies to certificates using PKCS or SCEP. Today, the SID is not embedded by issuing CAs using offline templates.

Azure Conditional Access

The short-lived certificate issued by Azure when Conditional Access is configured for Always On VPN did not include the SID. However, that recently changed.

Recent Updates

Today we can scratch Azure Conditional Access off the list of limitations for Always On VPN. Microsoft recently introduced support for the new SID extension in Azure Conditional Access certificates, as shown here.

Now when an Azure Conditional Access certificate is issued to an on-premises user or device account that is synced with Azure Active Directory, Azure Conditional Access will include the SID information in the issued short-lived certificate.

Intune

Unfortunately, we’re still waiting for Microsoft to address the limitation with certificates delivered using Microsoft Intune. Hopefully we’ll see an update for that later this year.

Additional Information

Certificate-Based Authentication Changes and Always On VPN

Microsoft KB5014754

Digital Certificates and TPM

Microsoft Intune Certificate Connector Service Account and PKCS

4 Comments

by Richard M. Hicks on July 11, 2023 • Permalink

Posted in AADJ, Active Directory, administration, Always On VPN, AOVPN, authentication, Azure, Azure Active Directory, Azure AD, Azure AD Join, Azure Conditional Access, Azure MFA, Azure VPN, Certificate Connector for Intune, certificates, cloud, Conditional Access, Deployment, Device Management, Endpoint Manager, Enterprise, enterprise mobility, HAADJ, Hybrid Azure AD Join, Infrastructure, Intune, Intune Certificate Connector, Intune PFX Connector, MDM, MEM, MEMCM, MFA, Microsoft, Microsoft Endpoint Manager, Microsoft Intune, Mobile Device Management, Mobility, Multifactor Authentiction, NDES, Network Device Enrollment Service, Network Device Enrollment Services, NPS, Operational Support, PFX Connector, PKCS, PKI, public cloud, public key infrastructure, Remote Access, SCEP, Security, Simple Certificate Enrollment Protocol, systems management, Update, user tunnel, VPN, Windows 10, Windows 11

Posted by Richard M. Hicks on July 11, 2023

https://directaccess.richardhicks.com/2023/07/11/azure-conditional-access-certificates-with-sid-information-now-available/

Always On VPN at MMSMOA 2023

I’m excited to share that I’ve been invited to present at the popular Midwest Management Summit at Mall of America (MMSMOA) this year! The event takes place Monday, May 2, through Thursday, May 4, 2023.

Sessions

I will be delivering two talks at the event this year. One on Microsoft Always On VPN and Intune, the other on deploying certificate using Intune.

Always On VPN and Intune: Notes from the Field – Tuesday, May 2 at 10:00 AM CDT

This session will cover all aspects of deploying and managing Always On VPN client configuration settings using Microsoft Intune.

Intune Certificate Management – Wednesday, May 3 at 10:00 AM CDT

This session will provide detailed configuration guidance and best practice recommendations for issuing on-premises enterprise PKI certificate using Microsoft Intune.

Attending MMS?

Will you be attending MMSMOA? Let’s connect! Drop in on my sessions, of course, but let’s plan to hang out! I will have copies of my book to give away too, so don’t miss out. Send me a note here or on Twitter, or just find me at the conference. Looking forward to seeing all of you soon!

Always On VPN at Workplace Ninja Summit 2022

The Workplace Ninja Summit takes place from 12-14 September 2022 in Lucerne, Switzerland. The conference focuses on endpoint management and security with platforms such as System Center Configuration Manager (SCCM) and Microsoft Endpoint Manager/Intune.

Conference Sessions

If you are participating in the conference, be sure to attend one of my sessions! I’m delivering the following three talks during the event.

Windows Always On VPN and Autopilot: Better Together

In this talk, I’ll cover in detail the critical aspects of implementing Always On VPN to support Autopilot provision with Intune.

Deploying On-premises Certificates with Intune

This session will explore the options for deploying enterprise PKI certificates using Intune. I’ll be sharing lots of security and implementation best practices.

Deploying Always On VPN with Intune: The Good, The Bad, and the Ugly

This talk will dive into the options for deploying Always On VPN using Intune. I’ll be covering many tips, tricks, and best practices and shining a light on many limitations and shortcomings of using Intune for Always On VPN.

Join Me!

Unfortunately, the conference is sold out, so if you haven’t made arrangements to attend you’ll have to wait until next year. If you are attending, please be sure to say hello!

Richard M. Hicks Consulting, Inc.

Microsoft MVP

TechMentor 2026

Consulting

Pluralsight

Newsletter

All posts in category Network Device Enrollment Services

Azure Conditional Access Certificates with SID Information Now Available