All posts in category Secure Socket Tunneling Protocol

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/

Always On VPN and the PSPKI PowerShell Module

Certificates are a crucial part of a secure Always On VPN implementation. Certificates are phishing-resistant forms of authentication that, when configured correctly, provide robust and multifactor authentication for remote access users and devices.

AD CS

Most commonly, certificates are issued by an on-premises Microsoft Active Directory Certificate Services (AD CS) server. Administrators configure and deploy a Certification Authority infrastructure to issue and manage user and device authentication certificates in their organization. CA certificates are also required on the VPN server to support Always On VPN device tunnel connections and IKEv2 user tunnel connections. The NPS server also requires an enterprise CA certificate. Of course, the CA can issue certificates for other purposes, including Wi-Fi authentication, document signing, and code signing, just to name a few.

PSPKI

PSPKI is a PowerShell module available in the PowerShell Gallery for configuring, managing, and troubleshooting Microsoft AD CS. Created by Vadims Podans of PKI Solutions, PSPKI includes over 100 functions for various AD CS and certificate-related tasks. Always On VPN administrators will find this PowerShell module helpful when configuring and troubleshooting certificate-related issues for their Always On VPN deployments.

Note: The AD CS remote server administration tools (RSAT) must be installed to access all of the PSPKI module’s functionality.

Installation

Run the following PowerShell command to install the PSPKI PowerShell module.

Install-Module -Name PSPKI

Always On VPN and PSPKI

Always On VPN Administrators will immediately find a few PSPKI functions helpful when implementing and supporting Always On VPN.

Test-WebServerSSL – This function will connect to a remote web server and display details about the TLS certificate included in the response. This can be especially helpful when troubleshooting SSTP VPN connections.

Convert-PfxToPem – This is a handy utility for converting a PFX file to the PEM format. This is commonly required when importing CA certificates on non-Microsoft platforms, security devices, and load balancers.

Convert-PemToPfx – Occasionally, administrators must convert a certificate and private key in PEM format to PFX to install on a Windows server. This tool allows administrators to perform this task easily.

Get-CertificationAuthority – This function quickly enumerates all enterprise CA servers and displays information about their hostname, accessibility, service status, and type.

Ping-ICertInterface – This function helps troubleshoot CA connectivity issues. Administrators can quickly determine if a CA is reachable and capable of issuing a certificate using this command.

Get-CaTemplate – This command displays a list of certificate templates published on the specified target CA server. The certificate template’s display name and the minimum support CA version are provided. In addition, the output indicates if certificate autoenrollment is enabled on the template.

Much More

The PSPKI PowerShell module for AD CS has many tools for configuring and managing AD CS. PSPKI recently received a major update to version 4.0. Download and install PSPKI today. It will make your life easier, I can assure you!

Additional Information

PSPKI PowerShell Module – PowerShell Gallery

PSPKI PowerShell Module – GitHub

AOVPNTools PowerShell Module – PowerShell Gallery

AOVPNTools PowerShell Module – GitHub

InboxAccountingDatabaseManagement PowerShell Module

InboxAccontingDatabaseManagement – PowerShell Gallery

InboxAccountingDatabaseManagement – GitHub

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by Richard M. Hicks on June 20, 2023  •  Permalink
Posted in Active Directory, administration, Always On VPN, AOVPN, authentication, certificates, Deployment, Encryption, Enterprise, enterprise mobility, GitHub, IKEv2, Infrastructure, Microsoft, Mobility, Multifactor Authentiction, NPS, Operational Support, PEAP, PKI, PowerShell, Protected EAP, public key infrastructure, Remote Access, routing and remote access service, RRAS, Secure Socket Tunneling Protocol, Security, SSL, SSL and TLS, SSTP, systems management, TLS, Transport Layer Security, troubleshooting, Update, user tunnel, VPN, Windows 10, Windows 11, Windows Server 2012 R2, Windows Server 2016, Windows Server 2019, Windows Server 2022
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Posted by Richard M. Hicks on June 20, 2023

https://directaccess.richardhicks.com/2023/06/20/always-on-vpn-and-the-pspki-powershell-module/

Always On VPN and VpnStrategy

NetMotion Mobility for DirectAccess Administrators – Split vs. Force Tunneling

Always On VPN supports a variety of VPN protocols for the user tunnel. Internet Key Exchange version 2 (IKEv2) and Secure Socket Tunneling Protocol (SSTP) are the most common. I wrote about the advantages and disadvantages of each in this post. To summarize, IKEv2 provides the highest security options but suffers from operational limitations. SSTP offers excellent security and is generally more reliable.

VpnStrategy

Always On VPN administrators must choose between IKEv2 and SSTP when configuring the Always On VPN user tunnel. Some administrators may prefer to use IKEv2 when available but then fall back to SSTP if it is not. To accomplish this requires editing the rasphone.pbk file and setting the value of VpnStrategy to 8, as described here.

Challenges

Unfortunately, setting the VpnStrategy value to 8 poses some challenges. Updating rasphone.pbk requires editing a text file on each endpoint post-deployment. Updating rasphone.pbk can be automated using the Update-Rasphone.ps1 script or Microsoft Intune proactive remediation.

Limitations

By default, Windows will overwrite the VpnStrategy setting in rasphone.pbk when fallback occurs. For example, setting VpnStrategy to prefer IKEv2 over SSTP will be reset to use SSTP first if a connection with IKEv2 fails. There’s a registry setting available that’s supposed to prevent this, but it doesn’t always work as expected.

Windows 11

There’s good news for administrators deploying Always On VPN on Windows 11. Microsoft recently introduced support for additional NativeProtocol types in XML. Specifically, VPN protocol preference can now be defined using the ProtocolList native protocol type. When using the ProtocolList native protocol type, each supported VPN protocol is listed in order of preference using the syntax shown below.

In addition, the RetryTimeInHours value defines the time Windows will try the last successful connection protocol. Setting this value to 0 overrides this and ensures the preferred protocol (the first protocol in the list) will always be attempted first.

SSTP Only

Previously the VPNv2CSP only supported IKEv2 or Automatic as values for the native protocol type. Windows 11 now supports SSTP as a native protocol type. Administrators configuring Always On VPN user tunnel connections using SSTP exclusively can now use this option.

Caveats

While the settings above are supported in both Windows 11 21H2 and 22H2, there are some known issues when enabling these settings. Specifically, when administrators define the ProtocolList value for the native protocol type, IKEv2 is always shown as the active protocol, even when an SSTP connection is established.

Also, if ProtocolList is used, the VPN connection cannot be managed using PowerShell. The VPN profile will not be displayed when running Get-VpnConnection at the time of this writing. Hopefully Microsoft will fix this soon.

Additional Information

Always On VPN CSP Updates

Always On VPN IKEv2 and SSTP Fallback

Always On VPN and Intune Proactive Remediation

Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN IKEv2 Features and Limitations

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by Richard M. Hicks on May 22, 2023  •  Permalink
Posted in administration, Always On VPN, AOVPN, Azure VPN, Deployment, Device Management, Enterprise, enterprise mobility, IKEv2, InTune, MDM, MEM, Microsoft, Microsoft Endpoint Manager, Microsoft Intune, Mobile Device Management, Mobility, Operational Support, PowerShell, Remote Access, Secure Socket Tunneling Protocol, Security, SSTP, systems management, user tunnel, VPN, Windows 11
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Posted by Richard M. Hicks on May 22, 2023

https://directaccess.richardhicks.com/2023/05/22/always-on-vpn-and-vpnstrategy/

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