Certificate-Based Authentication Changes and Always On VPN

Microsoft introduced important changes affecting certificate-based authentication on Windows domain controllers as part of the May 10, 2022 update KB5014754 that may affect Always On VPN deployments. The update addresses privilege escalation vulnerabilities when a domain controller is processing a certificate-based authentication request. The recommendation from Microsoft is that the update be applied to all Windows domain controllers and Active Directory Certificate Services (AD CS) servers as soon as possible.

Updated 5/20/2022: An out-of-band update to address authentication issues reported with this update is now available. Updates are available for Windows Server 2022, Windows Server 20H2, Windows Server 2019, Windows Server 2016, Windows Server 2012 R2, Windows Server 2012, Windows Server 2008 R2 SP1, and Windows Server 2008 SP2.

Certificate Services

After applying the update to certification authority (CA) servers, a non-critical extension with Object Identifier (OID) 1.3.6.1.4.1.311.25.2 is added to all issued certificates with the user or device security identifier (SID) included. Domain controllers with the update installed will use this information to validate the certificate used for authentication and ensure that it matches the information in Active Directory.

Domain Controllers

The update operates in Compatibility Mode, by default, when applied to domain controllers. Windows monitors authentication requests and records audit events for certificates presented for authentication under the following conditions.

No strong mapping (event ID 39) – The certificate has not been mapped explicitly to a domain account, and the certificate did not include the new SID extension.

Certificate predates account (event ID 40) – A certificate was issued before the user existed in Active Directory, and no explicit mapping could be found.

User’s SID does not match certificate (event ID 41) – A certificate contains the new SID extension, but it does not match the SID of the corresponding user account.

Certificate Mapping

Administrators can map certificates explicitly to accounts in Active Directory, but this results in a significant administrative burden in most environments. A better option is to reissue user and device authentication certificates after applying the KB5014754 update to all issuing CA servers.

Reenroll Certificates

Administrators should reissue user and device authentication certificates after applying the KB5014754 update. Open the Certificate Templates management console (certtmpl.msc), identify the user or device authentication certificate template, then right-click on the template and choose Reenroll All Certificate Holders.

Enforcement Mode

After applying update KB5014754, administrators should monitor domain controller event logs for event IDs 39, 40, and 41. Once all certificates have been updated, and none of these events have been recorded for 30 days, administrators can switch to Full Enforcement Mode by enabling it in the registry on all domain controllers.

Key: HKLM\SYSTEM\CurrentControlSet\Services\KDC
Value: StrongCertificateBindingEnforcement
Type: DWORD
Data: 2

Note: Microsoft will automatically switch to Full Enforcement Mode beginning May 9, 2023.

Known Issues

There have been some reports of authentication issues after installing the KB5014754 update. Early indications are that device authentication certificates missing a Subject Alternative Name (SAN) entry are to blame. Administrators are encouraged to update their device certificates to include the SAN entry. Optionally, but not recommended, administrators can place the update in disabled mode by editing the registry.

Note: An out-of-band update for these authentication issues is now available. See the reference links at the top of this article for more information.

Caveat

It’s important to understand that this new OID is added only to online templates. Online templates are those that build the subject information from Active Directory. Unfortunately, this new OID is NOT applied to offline templates (templates where the subject name is supplied in the request), such as those used for delivering certificates with Microsoft Endpoint Manager/Intune using PKCS or SCEP. It is impossible to move to enforcement mode when issuing user or device authentication certificates with Microsoft Endpoint Manager or Intune today. Microsoft is aware of this limitation and is working to address this issue as we speak. I expect a fix to be available sometime before the May 2023 deadline when Microsoft permanently switches on enforcement mode.

Additional Information

KB5014754 – Certificate-based authentication changes on Windows domain controllers

Microsoft Windows Always On VPN Users Prompted for Certificate

Microsoft Windows Always On VPN Clients Prompted for Authentication when Accessing Internal Resources

Always On VPN DPC Advanced Features

Recently I wrote about PowerON Platforms’ Always On VPN Dynamic Profile Configurator (DPC), a software solution that allows administrators to provision and manage Always On VPN client configuration settings using Active Directory and group policy. The article described the basic functionality Always On VPN DPC provides. In this post, I will describe some of its advanced capabilities that administrators will find helpful for solving common Always On VPN challenges.

Protocol Preference

The two most common VPN protocols used with Always On VPN are Internet Key Exchange version 2 (IKEv2) and Secure Socket Tunneling Protocol (SSTP). Each protocol has its advantages and disadvantages. For example, IKEv2 has better security options, but SSTP is more firewall-friendly and reliable.

IKEv2 with SSTP Fallback

Instead of selecting one protocol over the other, some administrators may choose to configure Always On VPN to prefer IKEv2, then fall back to SSTP if IKEv2 is unavailable. Unfortunately, there is no way to configure this using Intune, XML, or PowerShell. To change this setting, the administrator must update the VPN configuration file (rasphone.pbk) and change the value of VpnStrategy to 14. While editing a text file is easy, doing it at scale is more complicated. The setting can be changed using Intune proactive remediation or a PowerShell script. However, it’s even easier using Always On VPN DPC. Simply enable the VPN Protocol advanced setting in group policy and choose IKEv2 First, SSTP Fallback.

Interface Metric

Another common problem Always On VPN administrators encounter is name resolution, specifically when the endpoint uses a wired local connection. Here, name resolution queries may fail or return incorrect IP addresses. This happens because the wired connection has a lower network interface metric than the VPN tunnel adapter. Once again, there is no option for changing this setting using Intune or XML. Administrators can update the interface metrics using PowerShell, but it is not persistent. To fully resolve this, the administrator must edit the rasphone.pbk file. With Always On VPN DPC, enable the VPN Tunnel Metric group policy setting and enter a value lower than the wired connection to solve this problem.

IKE Mobility

The Windows VPN client includes support for IKE Mobility, which allows an IKEv2 VPN connection to reconnect automatically after a loss of network connectivity. IKE Mobility is enabled by default, and the network outage time is set to 30 minutes. However, this setting can have negative side effects, especially when VPN servers are behind a load balancer. Reducing the network outage time or disabling it completely can improve failover if a VPN server goes offline. Here again, this setting cannot be changed using Intune, XML, or PowerShell; it is only configurable in rasphone.pbk. With Always On VPN DPC, enable the Network Outage Time advanced setting in group policy and choose a value that meets your requirements.

Exclusion Routes for Office 365

Force tunneling ensures that all network traffic on the client is routed over the VPN tunnel, including Internet traffic. However, Always On VPN supports exclusion routes which allow administrators to exempt selected traffic from the VPN tunnel when force tunneling is enabled. Commonly this is configured for trusted cloud applications like Microsoft Office 365. Defining exclusion routes for cloud services is more complicated than it sounds. Many cloud services, including Microsoft Office 365, have multiple IP addresses that are constantly changing. This makes keeping Always On VPN clients updated with the correct list of IP address exclusions quite challenging. With Always On VPN DPC, administrators can enable the Exclude Office 365 from VPN group policy setting, allowing the endpoint to automatically configure the necessary exclusion routes for Office 365 IP addresses. Importantly, Always On VPN DPC periodically monitors this list of IP addresses and ensures that endpoints are continually updated with Office 365 exclusion routes as they change to ensure reliable connectivity.

IP Routing

Always On VPN administrators must define which IP addresses and networks are routed over the VPN tunnel when split tunneling is enabled. However, Intune has a known issue that may pose a challenge in some environments.

IPv6

Although IPv4 routes can be configured using the Intune UI, IPv6 routes cannot. This is because the Intune UI does not correctly validate the default IPv6 prefix length, insisting that the administrator use a value between 1 and 32. 🤦‍♂️

However, the Always On VPN DPC Allowed Routes group policy setting happily accepts the proper IPv6 prefix.

Route Metrics

In addition, there is no option to define the metric values for routes configured using Intune. Assigning non-default route metrics is required to resolve routing conflicts in some scenarios. Defining route metrics requires custom XML. The Always On VPN DPC Route Metric group policy settings allow administrators to define route metrics as required.

Video

I have published a demonstration video on my YouTube channel showing some of the advanced features PowerON Platforms Always On VPN Dynamic Profile Configurator (DPC) provides. Be sure to subscribe to stay up to date as I’ll be releasing more videos in the future.

Learn More

Are you interested in learning more about PowerON Platforms Always On VPN DPC? Fill out the form below, and I’ll contact you with more information. In addition, you can visit aovpndpc.com to register for an evaluation license.

Additional Information

Always On VPN with Active Directory and Group Policy

Always On VPN Video Demonstration

PowerON Platforms Always On VPN Dynamic Profile Configurator (DPC)

Always On VPN at MMSMOA 2022

I am excited to announce that I will be presenting at this year’s Midwest Management Summit at the Mall of America (MMSMOA) in Bloomington, Minnesota. The conference takes place the week of May 2. This is my first time presenting at this event, and I’m looking forward to sharing my experience deploying enterprise mobility and security infrastructure solutions with systems management professionals from around the world.

Sessions

I will be delivering three talks at the conference addressing various secure remote access and certificate services topics.

Managing Always On VPN with Intune

This session will provide administrators with everything they need to know about provisioning and managing Always On VPN client configuration settings using Intune. I’ll be providing tips, tricks, and best practices for Always On VPN profile configuration and demonstrating many of the limitations associated with using Intune. I will provide workarounds whenever possible.

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

Always On VPN Gateway Options in Azure

Deploying Always On VPN in Azure is increasingly common. However, administrators are unaware of the limitations of supporting Always On VPN connections with native Azure VPN gateway solutions. In this session, I’ll describe in detail what’s required to support Always On VPN and, importantly, what the limitations are.

Always On VPN Gateway Options in Azure

Deploying On-premises PKI Certificates with Intune

As organizations continue to migrate applications, services, and infrastructure to the cloud, the requirement for endpoints to be joined to an on-premises domain is fading. Moving to full Intune management and native Azure Active Directory join for endpoints is increasingly common. However, deploying enterprise PKI certificates o these endpoints is often required. This session will provide detailed guidance for choosing the best solution to deliver on-premises certificates to Azure AD joined devices using Intune.

Deploying on-premises PKI Certificates with Intune

Let’s Connect

I’m looking forward to meeting so many folks who have helped me get up to speed with Microsoft Endpoint Manager/Intune over the years. If you’re attending the conference, or if you are in the area, be sure to reach out. Let’s grab a beer and chat!

Additional Information

Midwest Management Summit at Mall of America (MMSMOA) 2022

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

Always On VPN Gateway Options in Azure

Deploying on-premises PKI Certificates with Intune

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