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Considerations for Always On VPN with Azure VPN Gateway and Virtual WAN

Always On VPN Device Tunnel and Custom Cryptography Native Support Now in Intune

Organizations migrating on-premises applications, data, and infrastructure to the cloud may also consider terminating Always On VPN connections there. Using one of the native Azure VPN services might be compelling at first glance. After all, having an Azure-managed VPN gateway service sounds intuitive. However, some severe limitations exist for using Azure VPN services for Always On VPN deployments.

Azure VPN Gateway

The following are limitations for Always On VPN with Azure VPN gateway.

Authentication Methods

Azure VPN gateway supports both EAP and machine certificate authentication. However, it can only support one authentication method at a time. With only EAP or certificate authentication, administrators must choose between a device or user tunnel. A single Azure VPN gateway cannot support both at the same time. For native Entra ID joined devices, this is not a problem. However, for native on-premises Active Directory or hybrid Entra ID joined devices, this is a problem, as the device tunnel is essential in these scenarios.

Note: Technically speaking, administrators could deploy another Azure VPN gateway to work around this limitation. However, Azure limits VPN gateway deployments to one per virtual network. This requires administrators to deploy a second VPN gateway in a separate virtual network, which then requires virtual network peering to be enabled, complicating the configuration greatly.

SSTP

Although the Azure VPN gateway supports SSTP, it is, unfortunately, a second-class citizen. Today, all SKUs of the Azure VPN gateway are limited to just 128 SSTP connections (256 in active/active mode). There is currently no way to increase this. If more than 256 connections are required, you must use IKEv2.

RADIUS

In addition, there is currently no option to change the default timeout value (30 seconds) for RADIUS authentication requests. This short timeout value presents a challenge when using MFA with the NPS extension or with Azure Conditional Access, as users may be unable to respond to the push notification before the timeout expires, resulting in failed authentication attempts.

In addition, Azure does not support routing traffic to on-premises RADIUS servers over ExpressRoute connections. In this scenario, administrators must route RADIUS traffic to on-premises servers over a site-to-site connection.

Geographic Redundancy

Geographic redundancy using Azure Traffic Manager (or another global server load balancer) with two or more gateways is not supported when using the Azure VPN gateway. Azure manages the certificate used on the gateway, which includes a certificate with the subject name of the individual gateway. There is no option to supply a custom certificate with a global hostname in the subject, which is required to support geographic redundancy. With that, administrators are limited to the redundancy provided natively by the Azure VPN gateway.

IPv6

Azure does not support Azure VPN gateway in a virtual network that includes IPv6 addressing.

Azure Virtual WAN

Azure Virtual WAN includes many of the same limitations as the Azure VPN gateway, in addition to the following.

SSTP

Unlike the Azure VPN gateway, there is no support for SSTP in Azure Virtual WAN.

IPv6

IPv6 is not currently supported at all in Azure Virtual WAN.

Summary

Intuitively, it seems that leveraging native Azure VPN gateway services would be ideal. However, due to the limitations outlined in this article, administrators must decide carefully if any of these prevent adoption in their environment. Although not formally supported, many organizations deploy Windows Server Routing and Remote Access (RRAS) servers in Azure to address these limitations.

Additional Information

Always On VPN Options for Azure Deployments

Always On VPN with Azure Gateway

Always On VPN Device Tunnel with Azure VPN Gateway

Always On VPN and RRAS in Azure

What is Azure VPN Gateway?

What is Azure Virtual WAN?

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by Richard M. Hicks on January 31, 2024  •  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 Virtual WAN, Azure VPN, Azure VPN Gateway, certificates, cloud, Cloud Service, Conditional Access, Deployment, device tunnel, EAP, Enterprise, enterprise mobility, Entra, Entra ID, extensible authentication protocol, global server load balancer, GSLB, HAADJ, High Availability, Hybrid Azure AD Join, IKEv2, Infrastructure, IPv6, MFA, Microsoft, Microsoft Entra, Microsoft Entra ID, Mobility, Multifactor Authentiction, multisite, network policy server, NPS, OTP, public cloud, Remote Access, routing and remote access service, RRAS, Secure Socket Tunneling Protocol, Security, SSTP, user tunnel, VPN, Windows 10, Windows 11, Windows Server 2016, Windows Server 2019, Windows Server 2022
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Posted by Richard M. Hicks on January 31, 2024

https://directaccess.richardhicks.com/2024/01/31/considerations-for-always-on-vpn-with-azure-vpn-gateway-and-virtual-wan/

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

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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
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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 Book Available for Pre-Order

Great news! My new book, Implementing Always On VPN, is now available for pre-order on Amazon.com. This new book, scheduled for release in late 2021, is a comprehensive implementation guide for Windows 10 Always On VPN. Drawing on many years of experience deploying Always On VPN for organizations worldwide, it covers all aspects of an Always On VPN deployment, including planning and design, prerequisite gathering, infrastructure preparation, and client deployment.

In addition, it contains detailed, prescriptive guidance for advanced configuration options such as application and traffic filtering and proxy server configuration. Cloud deployments using Azure VPN gateway and Virtual WAN are covered, and it includes guidance for configuring Azure MFA and Conditional Access.

Also, the book includes thorough guidance for provisioning certificates using Microsoft Endpoint Manager/Intune using both PKCS and SCEP. It outlines options for high availability for VPN and authentication infrastructure and provides details for ongoing system maintenance and operational support.

Finally, the book has an entire chapter dedicated to troubleshooting and resolving common (and not so common!) issues encountered with Windows 10 Always On VPN.

Reserve your copy today. Pre-order Implementing Always On VPN now!

Chapter List

  1. Always On VPN Overview
  2. Plan an Always On VPN Deployment
  3. Prepare the Infrastructure
  4. Configure Windows Server for Always On VPN
  5. Provision Always On VPN clients
  6. Advanced Configuration
  7. Cloud Deployments
  8. Deploy Certificates with Intune
  9. Integrating Azure MFA
  10. High Availability
  11. Monitor and Report
  12. Troubleshooting
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by Richard M. Hicks on September 27, 2021  •  Permalink
Posted in Always On VPN, Always On VPN Book, AOVPN, AOVPN Book, authentication, Azure, Azure Active Directory, Azure AD, Azure Conditional Access, Azure MFA, Azure Virtual WAN, Azure VPN, Azure VPN Gateway, certificates, cloud, Conditional Access, Device Management, device tunnel, education, Endpoint Manager, Enterprise, enterprise mobility, High Availability, InTune, Intune Certificate Connector, Intune PFX Connector, learning, Load Balancing, MFA, Microsoft Endpoint Manager, Microsoft Intune, Mobility, Multifactor Authentiction, NDES, Network Device Enrollment Services, network policy server, NPS, Operational Support, PFX Connector, PKI, PowerShell, ProfileXML, public cloud, public key infrastructure, Recommended Reading, Remote Access, reporting, routing and remote access service, RRAS, SCCM, SCEP, Security, Simple Certificate Enrollment Protocol, System Center Configuration Manager, systems management, Traffic Filter, user tunnel, VPN, Windows 10, Windows 11, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019, Windows Server 2022, Zero Trust, Zero Trust Network Access, ZTNA
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Posted by Richard M. Hicks on September 27, 2021

https://directaccess.richardhicks.com/2021/09/27/always-on-vpn-book-available-for-pre-order/

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