All posts tagged Azure

Always On VPN and Azure VPN Gateway SSTP Protocol Retirement

The Azure VPN gateway has been an option for supporting Microsoft Always On VPN client connections for organizations moving resources to the cloud. Today, Azure VPN gateway supports Internet Key Exchange version 2 (IKEv2), OpenVPN, and Secure Socket Tunneling Protocol (SSTP), although SSTP support has long been limited in scope and scalability. However, Microsoft recently indicated that some important changes are coming soon that will affect VPN protocol support on the Azure VPN gateway.

SSTP and Azure VPN Gateway

Microsoft has announced plans to deprecate and eventually remove support for SSTP on the Azure VPN gateway.

Key Dates

Here is Microsoft’s timeline for retiring SSTP for VPN connections.

  • March 31, 2026 – SSTP can no longer be enabled on new or existing gateways
  • March 31, 2027 – Existing SSTP connections will stop functioning

SSTP: Second Class Citizen

The retirement of SSTP for Azure VPN gateway should not have a significant impact on Always On VPN deployments. Support for SSTP on Azure VPN gateway has always been limited, making it a less viable option for most Always On VPN deployments. SSTP connections are capped at 128 concurrent connections (256 in active-active mode), regardless of gateway SKU. Additionally, Azure VPN gateway does not support simultaneous user and device tunnels, further limiting its usefulness in modern Always On VPN designs.

Plan Migration Now

If you are using Azure VPN gateway to support Always On VPN client connections, now is the time to begin planning a migration to IKEv2, which offers better scalability and native Always On VPN support. Alternatively, consider Windows Server RRAS in Azure, a third-party VPN solution, or Entra Private Access if Azure VPN gateway no longer meets your requirements.

More Information

For official guidance, see SSTP Protocol Retirement and Connections Migration. If you’re unsure how this change affects your Always On VPN deployment, or you would like help planning a migration, this is a good time to review your design and roadmap. Fill out the form below, and I’ll provide you with more information.

Additional Information

SSTP Protocol Retirement and Connections Migration

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

Windows Server RRAS in Microsoft Azure

Microsoft Entra Private Access

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by Richard M. Hicks on January 26, 2026  •  Permalink
Posted in Always On VPN, Azure and AWS, Windows Server
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Posted by Richard M. Hicks on January 26, 2026

https://directaccess.richardhicks.com/2026/01/26/always-on-vpn-and-azure-vpn-gateway-sstp-protocol-retirement/

Microsoft Entra Private Network Connector Overview and Deployment Strategies

When deploying Microsoft Entra Private Access, administrators must install at least one Entra Private Network Connector to facilitate communication between Global Secure Access clients and on-premises resources. The Entra Private Network connector is a software agent that communicates outbound only. It requires no inbound connectivity, reducing public network exposure and minimizing the organization’s attack surface.

Entra Private Network Connector

The Entra Private Network connector is essentially Microsoft Entra application proxy (formerly Azure AD Application Proxy), updated to support all TCP and UDP-based communication. You can download the connector by opening the Entra admin center, navigating to Global Secure Access > Connect > Connectors, and clicking the Download connector service link.

Cloud Appliances

To enable access to cloud-hosted resources, the Entra Private Network connector can be installed on a VM in those environments. However, the Entra Private Network connector is also available as an appliance in public preview for the following cloud providers.

Resource Requirements

The following recommendations pertain to VM resources for the Entra Private Network connector server.

  • Windows Server 2016 or later. However, Windows Server 2016 reaches end of life in January 2027, so Windows Server 2022 and later are recommended. The Desktop edition is required, but it can technically be installed on Server Core with the Application Compatibility Feature on Demand for Server Core. However, Microsoft may not formally support this option.
  • Minimum 4 CPU cores and 8GB RAM. Monitor resource utilization during migration. Provision additional CPU and/or memory when utilization consistently exceeds 70% during peak times. Scaling out (adding servers) is preferred over scaling up (adding CPU and RAM).
  • Domain Join. Domain join is optional but recommended. Domain join is required to support single sign-on (SSO).

Connector Groups

A Connector Group is a logical grouping of Entra Private Network connectors. A Connector Group functions as a single unit for high availability and load balancing. Connectors are deployed in the same region as the tenant by default.

Default Group

When you install the Entra Private Network connector, it is placed into the Default connector group. However, this may not always be desirable. For example, the organization may have multiple data centers in different geographies. They may also have resources hosted in different Active Directory forests or perhaps located in isolated network locations. Using a common connector group may be suboptimal or not work at all.

Custom Groups

Administrators can define custom connector groups as needed. Custom connector groups ensure that connectors always have access to the resources nearest to them. They can be deployed in different locations and assigned to other Azure regions to ensure optimal traffic routing and reduced latency. Today, administrators can create connector groups in the North America, Europe, Australia, Asia, and Japan regions.

Create a Connector Group

Open the Microsoft Entra admin center and perform the following steps to create a new Entra Private Network connector group.

  1. Navigate to Global Secure Access > Connect > Connectors and Sensors.
  2. Click on New Connector Group.
  3. In the Name field, enter a descriptive name for the connector group.
  4. From the Connectors drop-down list, select one or more Entra Private Network connectors to assign to the group. Optionally, you can leave this field blank and assign connectors later.
  5. Click Save.
Entra admin center New Connector Group page with name and connector selection

Connector Group Assignment

Once you have created a new connector group, you can assign Quick Access or individual Enterprise applications to it as follows.

Quick Access

To assign a new connector group to the Quick Access application, open the Entra admin console, navigate to Global Secure Access > Applications > Quick Access, and select the Network access properties tab. Select the new connector group from the Connector Group drop-down list.

Quick Access network access properties with the Connector Group drop-down list

Enterprise Applications

To assign a new connector group to an individual Enterprise application, navigate to Global Secure Access > Applications > Enterprise applications. Select an application, then select Network access properties. Select the new connector group from the Connector Group drop-down list.

Enterprise application network access properties with the Connector Group drop-down list

Deployment Strategy

The following are best practices for deploying the Entra Private Network connector.

Redundancy

Always deploy at least two Entra Private Network connectors to ensure high availability and eliminate single points of failure.

Location

Install the Entra Private Network connector on servers closest to the applications they serve. Deploy connectors in all locations where applications are accessed, including on-premises networks and Infrastructure-as-a-Service (IaaS) resources.

Default Connector Group

Avoid using the default connector group for application assignment. Always use custom connector groups for application access. This ensures that new connectors do not process production traffic immediately after installation, which can cause unexpected behavior if the connector is not optimally deployed for the published resource or is not connected to the back-end application.

Deleting Connectors

Entra Private Network connectors cannot be removed from the management console. If you uninstall a connector, its status will show as inactive. After 10 days of inactivity, it will be automatically removed.

Reassigning Connectors

Administrators can reassign connectors to different connector groups at any time. However, existing connections on that connector server from the prior group assignment will remain until they age out. Administrators can restart the connector service or reboot the server to address this issue.

Restart-Service -Name WAPCSvc -PassThru

Connector Updates

The Entra Private Network connector will automatically install major updates when they become available. However, not all updates are applied automatically. Don’t be alarmed if you see discrepancies between release versions across multiple connector servers in the admin console. Administrators can always perform software updates manually to ensure uniform connector versions in their environment, if desired.

Diagnostics

Beginning with Entra Private Network connector v1.5.4287.0, the agent installation also includes the diagnostic utility ConnectorDiagnosticsTool.exe, which is in the C:\Program Files\Microsoft Entra Private Network Connector\ folder on the connector server. Running the tool initiates a series of tests to perform a health check of the connector service, including certificate status, connectivity, enabled TLS versions, service status, and more.

ConnectorDiagnosticsTool.exe health check results for the Entra Private Network connector

Note: Entra Private Network connector v1.5.4522.0 and later includes a graphical output, as shown above. Previous versions featured text-based output only.

Summary

Microsoft Entra Private Network Connectors are lightweight, outbound-only agents that enable secure access to on-premises and cloud resources through Entra Private Access. Best practices emphasize deploying at least two connectors per location for redundancy, placing them close to target applications, using custom connector groups for high availability, load balancing, and optimal routing, and assigning them to Quick Access or enterprise applications while avoiding the default group. Ensure that VMs are appropriately sized for the expected connector traffic, and consider using marketplace appliances for Azure, AWS, and GCP. If you’ve previously deployed the Entra Private Network connector, ensure that it is running the latest release to take advantage of new diagnostics for troubleshooting.

Additional Information

Microsoft Entra Private Network Connectors

Microsoft Entra Private Network Connector groups

Preventing Port Exhaustion on Entra Private Network Connector Servers

Microsoft Entra Private Access Intelligent Local Access

Always On VPN vs. Entra Private Access: Choosing the Right Access Model

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by Richard M. Hicks on January 19, 2026  •  Permalink
Posted in Azure and AWS, Entra Global Secure Access, Entra ID, Entra Private Access, Windows Server, Zero Trust and SSE
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Posted by Richard M. Hicks on January 19, 2026

https://directaccess.richardhicks.com/2026/01/19/microsoft-entra-private-network-connector-overview-and-deployment-strategies/

Free Entra Certificate-Based Authentication Training Course

I’m pleased to announce I’ll present a FREE online training course on Microsoft Entra Certificate-Based Authentication (CBA). The course will be delivered through the ViaMonstra Online Academy on Wednesday, November 6, beginning at 10:00 AM CST. Once again, this training course is entirely FREE, so don’t hesitate to register now! If you can’t attend the live session, you can always view the presentation recording later.

Course Highlights

Join me for this 90-minute live, online training session where you will learn:

  • How certificate-based authentication offers more robust protection than passwords alone and mitigates phishing and MFA bypass risks
  • How Entra CBA enables a seamless, passwordless user experience while maintaining high security and assurance
  • How Entra CBA eliminates the need for physical authentication devices such as FIDO keys or security tokens, reducing costs and complexity
  • How to configure and manage affinity binding and authentication strength policies for Entra CBA

When you attend the live event, you’ll have the opportunity to ask questions directly during the presentation, so be sure to register today and join us for this free training session!

Additional Information

Microsoft Entra Certificate-Based Authentication (CBA)

Mini-Course – Microsoft Entra Certificate-Based Authentication

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by Richard M. Hicks on October 14, 2024  •  Permalink
Posted in Authentication and MFA, Certificate-Based Authentication, Cloud PKI, Conditional Access, Cryptography, Entra ID, Microsoft Intune, NDES and SCEP, PKI, Training and Events
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Posted by Richard M. Hicks on October 14, 2024

https://directaccess.richardhicks.com/2024/10/14/free-entra-certificate-based-authentication-training-course/

Cloud PKI for Microsoft Intune on RunAs Radio

Recently, I joined my good friend Richard Campbell on his popular RunAs Radio podcast. In this episode, we discussed Microsoft’s new Cloud PKI for Intune service. Cloud PKI for Intune is a PKI-as-a-service solution that allows organizations to issue and manage digital certificates without deploying on-premises infrastructure. Optionally, Cloud PKI for Intune supports integration with an existing on-premises PKI. Cloud PKI for Intune isn’t without a few drawbacks, though. We discuss all the benefits and limitations during this podcast, so be sure to listen!

Additional Information

Cloud PKI for Microsoft Intune on RunAs Radio Episode 943

Overview of Cloud PKI for Microsoft Intune

Cloud PKI for Microsoft Intune and Active Directory

Cloud PKI for Microsoft Intune SCEP URL

Cloud PKI for Microsoft Intune and Certificate Templates

2 Comments
by Richard M. Hicks on July 31, 2024  •  Permalink
Posted in Authentication and MFA, Certificate-Based Authentication, Cloud PKI, Cryptography, Entra ID, Intune Certificate Connector, Microsoft Intune, NDES and SCEP, PKI
Tagged , , , , , , , , ,

Posted by Richard M. Hicks on July 31, 2024

https://directaccess.richardhicks.com/2024/07/31/cloud-pki-for-microsoft-intune-on-runas-radio/

Microsoft Cloud PKI for Intune SCEP URL

Earlier this year, Microsoft announced Cloud PKI for Intune, a cloud service for issuing and managing digital certificates for Intune-managed endpoints. With Cloud PKI for Intune, administrators no longer need to deploy on-premises infrastructure to use certificates for user and device-based authentication for workloads such as Wi-Fi and VPN. Cloud PKI for Intune can be used standalone (cloud native) or integrated with an existing on-premises Active Directory Certificate Services (AD CS) enterprise PKI to extend an existing on-premises certificate services infrastructure.

Provisioning

Cloud PKI for Intune utilizes Simple Certificate Enrollment Protocol (SCEP) to enroll certificates for users and devices. To deploy Intune Cloud PKI certificates, administrators must create and deploy a SCEP Certificate device configuration policy in Intune.

SCEP URL

When creating the SCEP certificate device configuration policy in Intune, administrators are asked to supply the SCEP server URL. Administrators will find this information by opening the Intune management console, navigating to Tenant Administration > Cloud PKI, clicking on the issuing certification authority, and then clicking Properties.

Administrators may notice the URL is unreachable if they try to connect to it using their web browser or PowerShell. Specifically, the FQDN is not shown in the URI; instead, it is represented as the variable {{CloudPKIFQDN}}, as highlighted above.

Policy Configuration

You can safely ignore this as it is not an error or misconfiguration. Simply copy and paste the entire URL into your SCEP certificate device configuration profile as is. Intune in the background will convert this to a fully formed URL with a proper FQDN accessible from the public Internet. This variable is used because it allows Microsoft to use different resources dynamically according to geography and availability.

Additional Information

RFC 8894 – Simple Certificate Enrollment Protocol

Microsoft Cloud PKI for Intune

Microsoft Cloud PKI for Intune and Active Directory

Microsoft Cloud PKI for Intune and Certificate Templates

2 Comments
by Richard M. Hicks on June 25, 2024  •  Permalink
Posted in Authentication and MFA, Certificate-Based Authentication, Cloud PKI, Cryptography, Entra ID, Intune Certificate Connector, Microsoft Intune, NDES and SCEP, PKI, Windows Server
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Posted by Richard M. Hicks on June 25, 2024

https://directaccess.richardhicks.com/2024/06/25/microsoft-cloud-pki-for-intune-scep-url/

Microsoft DirectAccess Formally Deprecated

Today, Microsoft has announced the formal deprecation of DirectAccess. Microsoft DirectAccess is a widely deployed enterprise secure remote access solution that provides seamless, transparent, always-on remote network connectivity for managed (domain-joined) Windows clients. First introduced in Windows Server 2008 R2, it’s been a popular solution with many advantages over ordinary VPN technologies of the past.

Windows Server 2012

DirectAccess was almost entirely rewritten in Windows Server 2012. Many of the features and enhancements offered for DirectAccess with the Unified Access Gateway (UAG – a separate product with additional costs) were built into the operating system directly. In addition, Microsoft introduced integrated load balancing and geographic redundancy features.

Demise of DirectAccess

DirectAccess relies heavily on classic on-premises technologies like Active Directory. All DirectAccess servers and clients must be joined to a domain. In addition, all DirectAccess clients must be running the Enterprise edition of Windows. With organizations rapidly adopting cloud services such as Azure and Entra ID, Microsoft began to develop an alternative solution that better integrated with the cloud. That solution is Always On VPN. With that, Microsoft stopped developing DirectAccess after the release of Windows Server 2012 R2. No new features or capabilities have been added to DirectAccess since that time.

Deprecation

We’ve been speculating about the end of life for DirectAccess for quite some time now. However, this formal deprecation announcement from Microsoft is official. It is the end of the road for this technology. To be clear, though, DirectAccess is available today in Windows Server 2022 and Windows 11. DirectAccess will be included in the upcoming release of Windows Server 2025. However, formal deprecation from Microsoft means they will remove DirectAccess components from the next release of the operating system.

What Happens Now?

Organizations should begin formal planning efforts to migrate away from DirectAccess. Here are a few popular solutions to consider.

Always On VPN

Always On VPN is the direct replacement for DirectAccess. It was designed to provide feature parity for DirectAccess, with seamless, transparent, always-on remote network connectivity. However, Always On VPN better integrates with Entra ID and supports conditional access. It does not require domain-joined devices or servers and works well with cloud-native endpoints. Always On VPN is a good choice for organizations that employ hybrid Entra-joined devices.

Entra Private Access

Entra Private Access, part of the Entra Global Secure Access suite, is an identity-centric zero-trust network access (ZTNA) solution from Microsoft. It is in public preview now and has some compelling advantages over traditional VPNs. However, Entra Private Access is not feature complete today. In addition, it is best suited to cloud-native (Entra-joined only) endpoints.

Absolute Secure Access

Absolute Secure Access (formerly NetMotion Mobility) is a premium enterprise remote access solution with many advanced options. It is by far the best solution on the market today. Absolute Secure Access is a software solution that supports zero-trust configuration and includes many features to improve and enhance security, performance, and visibility. In addition, it provides cross-platform support, including Windows, macOS, iOS, and Android operating systems.

Learn More

We have several decades of experience working with secure remote access technologies. We can help you and your organization find the best solution for your needs. Fill out the form below for a free one-hour consultation to discuss your DirectAccess migration strategy today.

Additional Information

Deprecated Features for Windows Client

1 Comment
by Richard M. Hicks on June 12, 2024  •  Permalink
Posted in Absolute Secure Access, Always On VPN, Conditional Access, Consulting Services, DirectAccess, Entra Global Secure Access, Entra ID, Entra Private Access, Microsoft Intune, Windows Server, Zero Trust and SSE
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Posted by Richard M. Hicks on June 12, 2024

https://directaccess.richardhicks.com/2024/06/12/microsoft-directaccess-formally-deprecated/

Microsoft Intune Cloud PKI

Recently, Microsoft introduced the general availability of its new PKI-as-a-service solution called Microsoft Intune Cloud PKI. Cloud PKI allows administrators to issue and manage user and device authentication certificates for Intune-managed endpoints without deploying Active Directory Certificate Services (AD CS) on-premises. Cloud PKI frees administrators from the burdens of deploying and managing AD CS, including the complicated Network Device Enrollment Service (NDES) server configuration required for Simple Certificate Enrollment Protocol (SCEP) certificate deployment with Intune.

Advantages

Microsoft Intune Cloud PKI offers many significant advantages over traditional on-premises AD CS deployments.

No Infrastructure

The most obvious advantage of using Cloud PKI is that you do not have to deploy and manage your own Certification Authority (CA). Although implementing AD CS isn’t that difficult, managing and operating a CA infrastructure securely can be quite challenging. In addition, a high-security AD CS deployment utilizes hardware secure modules (HSMs) to protect CA private keys, which are quite expensive and sometimes difficult to support.

Cloud-Hosted SCEP

Removing the requirement to configure and deploy your own NDES server to support SCEP certificates is certainly a welcome advantage. NDES is notoriously difficult to configure, secure, and troubleshoot when it doesn’t work correctly. Cloud PKI includes cloud hosted SCEP services that are highly available and redundant within the Microsoft Azure infrastructure.

Automatic Revocation

Cloud PKI automates the deployment of certificates to Intune-managed users and devices and automatically revokes certificates when they fall out of scope. Administrators can also manually revoke certificates using the Intune management console.

Reporting

Administrators can easily view the status of Cloud PKI-issued certificates in Intune. The UI shows the active, expired, and revoked certificates for the issuing CA.

Clicking View all certificates shows a detailed list of all certificates.

BYOCA

Another compelling feature of Cloud PKI is Bring Your Own CA (BYOCA). This feature enables administrators to deploy a cloud-hosted CA that is chained to their existing on-premises AD CS root CA. This is helpful for scenarios where AD CS is already in place and used to issue and manage certificates to existing domain-joined clients and servers. BYOCA effectively allows you to extend your existing CA infrastructure to the cloud and use Cloud PKI to issue and manage certificates for your Intune-managed endpoints while maintaining the full functionality and feature set of on-premises AD CS for non-Intune-managed devices.

Limitations

Although there are many advantages to Cloud PKI, there are some limiting factors to consider.

RSA Only

Today, Cloud PKI is limited to RSA keys only. Administrators can create CAs using RSA 2048, 3072, or 4096-bit keys. Elliptic Curve (EC) keys are not currently supported in Cloud PKI.

Intune Devices Only

Cloud PKI is limited to issuing certificates to Intune-managed devices only. Endpoints must be Entra-joined, or hybrid Entra-joined to enroll for certificates using Cloud PKI.

Inflexible Configuration

The Cloud PKI root and issuing CAs cannot be reconfigured after deployment. Since Cloud PKI root and issuing CAs don’t support the Any Purpose EKU (2.5.29.37.0), all EKUs must be defined when the CA is created. If, in the future, an administrator requires an EKU that was not present when the CA was deployed, an entirely new hierarchy (root and issuing CA) must be deployed.

Cost

There’s been much discussion about the cost associated with Cloud PKI. Cloud PKI can be licensed as part of the Intune Suite, which is $10.00 per user per month. Cloud PKI licenses will also be available as a standalone add-on for $2.00 per user per month. For large organizations, this might be cost-prohibitive.

Summary

Overall, Microsoft Intune Cloud PKI is a welcome addition to the Microsoft suite of cloud services. Certificates are excellent phishing-resistant credentials that can be used to improve security for organizations of all sizes. However, managing a CA can be tedious and time-consuming. Leveraging the cloud for PKI and certificate management will be helpful in many scenarios. However, Cloud PKI has some potential drawbacks, and many may not fit everyone.

More Information

Want to learn more about Microsoft Intune Cloud PKI and how it can benefit your organization? Take the first step towards streamlined certificate management and enhanced security for your organization. Fill out the form below, and I’ll provide more information about using Intune Cloud PKI to safeguard your digital assets confidently.

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Thank you for your response. ✨

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by Richard M. Hicks on March 18, 2024  •  Permalink
Posted in Authentication and MFA, Certificate-Based Authentication, Cloud PKI, Cryptography, Entra ID, Intune Certificate Connector, Microsoft Intune, NDES and SCEP, NPS and EAP, PKI, Windows Server
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Posted by Richard M. Hicks on March 18, 2024

https://directaccess.richardhicks.com/2024/03/18/microsoft-intune-cloud-pki/

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?

3 Comments
by Richard M. Hicks on January 31, 2024  •  Permalink
Posted in Always On VPN, Authentication and MFA, Azure and AWS, Conditional Access, Entra ID, IPv6, Load Balancing, NPS and EAP, PKI, Windows Server
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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/

Microsoft Entra Global Secure Access

Last week Microsoft introduced new Security Service Edge (SSE) capabilities as part of the Microsoft Entra suite of technologies. Included in these announcements, Microsoft introduced the public preview of two new secure remote access technologies – Microsoft Entra Internet Access and Microsoft Entra Private Access. The latter of these will particularly interest Microsoft Always On VPN administrators in some deployment scenarios.

Microsoft Entra Internet Access

Microsoft Entra Internet Access is a new Secure Web Gateway (SWG) cloud service solution designed to protect users from threats on the public Internet. Features include web content filtering, malware inspection, TLS inspection, and more. In addition, Entra Internet Access can protect Microsoft 365 applications. Azure Conditional Access policies can be enforced for Internet traffic. Network conditions are now included with Azure Conditional Access, which can further protect against attacks by requiring access from specific trusted or compliant networks. Today, the public preview is available for Microsoft 365 scenarios only. Internet traffic and other SaaS applications will be available later this year.

Microsoft Entra Private Access

Microsoft Entra Private Access is a Zero Trust Network Access (ZTNA) cloud service solution that leverages the Azure Application Proxy access model. With Azure App Proxy, administrators can easily publish private, on-premises web applications by installing the connector on an on-premises server. Administrators can leverage Azure AD authentication and conditional access policies to ensure device compliance or enforce multifactor authentication (MFA), if required. Microsoft Entra Private Access extends the capabilities of the Azure Application Proxy to support TCP and UDP-based applications.

Private Access vs. Always On VPN

Microsoft Entra Private Access will be a compelling alternative to Always On VPN in the future. Specifically, organizations using native Azure AD join devices could benefit tremendously from this technology. Microsoft Entra Private Access is much simpler to implement than Always On VPN and requires no on-premises infrastructure other than the Azure Application Proxy connector. Using Microsoft Entra Private Access also means that no inbound access from the Internet is required, making the solution inherently more secure and reducing the public attack surface. For organizations using hybrid Azure AD join, Always On VPN continues to be the best Microsoft solution for these scenarios.

References

Microsoft Entra Expands into Security Service Edge (SSE)

Microsoft Entra – Secure Access for a Connected World

Microsoft Entra Internet Access Preview

Microsoft Entra Private Access Preview

What is Zero Trust?

What is Zero Trust Network Access?

What is Security Service Edge (SSE)?

What is Secure Access Service Edge (SASE)?

What’s the Difference Between SSE and SASE?

Contact Us

I’ve had the privilege of participating in the private preview for Microsoft Entra Internet Access and Private Access. If you’d like to learn more about these technologies and how they can help your organization, fill out the form below, and I’ll provide more information.

8 Comments
by Richard M. Hicks on July 17, 2023  •  Permalink
Posted in Always On VPN, Authentication and MFA, Conditional Access, Entra ID, Entra Internet Access, Entra Private Access, Zero Trust and SSE
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Posted by Richard M. Hicks on July 17, 2023

https://directaccess.richardhicks.com/2023/07/17/microsoft-entra-global-secure-access/

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 Always On VPN, Authentication and MFA, Conditional Access, Entra ID, Intune Certificate Connector, Microsoft Intune, NDES and SCEP, NPS and EAP, PKI, Security Updates, Windows Server
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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/

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