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

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

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/

Microsoft Intune Certificate Connector Failure

The Microsoft Intune Certificate Connector enables the provisioning and de-provisioning of on-premises PKI certificates for Intune-managed devices. Always On VPN administrators using Intune to deploy certificates with the Intune Certificate Connector using either PKCS or SCEP may encounter a scenario where certificates are no longer being provisioned to users or devices after working reliably previously.

Certificate Not Found

When this issue occurs, users will no longer be able to access the VPN and receive a “certificate could not be found that can be used with this Extensible Authentication Protocol” error message.

Connector Status

To determine the status of the Intune Certificate Connector, open the Microsoft Intune Admin Center (https://intune.microsoft.com) and navigate to Tenant Administration > Connectors and Tokens > Certificate Connectors. The status of the certificate connector server will be in Error.

Event Log

Open the event log on the server where the Intune Certificate Connector is installed. Navigate to Applications and Services Logs > Microsoft > Intune > CertificateConnectors > Operational. Here, you will find a variety of warning and error messages.

Event ID 5001

This is a warning from the CertificateConnectors source with event ID 5001 in the Task Category HealthMessageUploadFailedAttempt with the following details.

PKI Create Service:

Failed to upload health messages. Requeuing messages.

Event ID 1003

This is an error from the CertificateConnectors source with event ID 1003 in the Task Category PkcsDownloadFailure with the following details.

PKI Create Service:

Failed to download PKCS requests.

Event ID 2

This is an error from the CertificateConnectors source with event ID 2 in the Task Category Exception with the following details.

PKI Create Service:

Microsoft.Intune.Connectors.PkiCreateProcessor.Process threw an exception.

Expired Certificate

The warning and error messages recorded in the event log indicate an expired certificate on the Intune Certificate Connector server. Open the local computer certificate store (certlm.msc) on the server where the Intune Certificate Connector is installed. Review the expiration date of the certificate issued by Microsoft Intune ImportPFX Connector CA. It is most likely expired.

Click on the Certification Path tab to view the certificate status.

Renew Certificate

To renew this certificate, you must reinstall the Intune Certificate Connector. However, you do not have to uninstall it first. To renew the certificate, navigate to C:\Program Files\Microsoft Intune\PFXCertificateConnector\ConnectorUI and double-click on PFXCertificateConnectorUI.exe. Follow the prompts without making changes to the existing configuration. You’ll be prompted for the service account password (if using a domain account) and proxy credentials (if using a proxy server). In addition, you’ll be asked to sign in to Entra ID (formerly Azure AD). Be sure to provide credentials that are a global administrator and have an Intune license assigned. Once the process is complete, a new certificate will be installed in the local computer certificate store.

Intune Configuration

After updating the Intune Certificate Connector, a new certificate connector appears in the Intune Admin Center. You can now safely delete the old connector and rename the new one accordingly.

Redundancy

Deploying multiple instances of the Intune Certificate Connector is an excellent way to avoid future outages! It’s also a good idea to stagger their installation by a few months to ensure that a future certificate expiration doesn’t result in lost functionality. If you’ve deployed Intune Certificate Connectors recently, consider updating them at rotating intervals so certificates expire at different times.