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

Always On VPN at TechMentor 2023

I’m excited to announce that I’ll be presenting at this year’s TechMentor IT training conference! The event takes place July 17-21, 2023, at the Microsoft headquarters in Redmond, Washington.

My Sessions

I will be delivering two talks at this year’s event.

TT04 – Deploying On-premises Certificates using Intune

In this talk, I’ll describe in detail how to deliver on-premises enterprise PKI certificates using Intune. We’ll cover all aspects of certificate delivery, including the Intune Certificate Connector configuration, device configuration profile options, advantages of PKCS over SCEP, and certificate template security best practices.

TT07 – Windows Always On VPN: Notes from the Field

During this session, I’ll share many tips, tricks, and best practices for deploying and managing Always On VPN client configuration settings using Intune. I’ll explain the limitations of the Intune VPN profile template and how to work around them using custom XML. I will also describe how to use Intune Proactive Remediation to optimize Always On VPN client configuration settings post deployment.

Discount Code

Use the discount code Hicks and receive $400.00 off the standard pricing for the event. Don’t miss out on this opportunity to learn from some of the best IT pros in the business. Register today!

Let’s Connect!

If you’re attending TechMentor 2023 this year, let’s connect! I’ll be at the conference all week. Attend one of my sessions, join me on Thursday for a Table Topic lunch, or let’s grab a beer somewhere. Reach out to me and arrange some time!