Always On VPN and RRAS on Windows Server Core

Windows Server Core is a refactored version of the full Windows Server operating system. Server Core does not include a Graphical User Interface (GUI) and must be managed via the command line or with PowerShell. The Routing and Remote Access Service (RRAS) is a supported workload on all supported versions of Windows Server including Windows Server 2022. Always On VPN administrators should consider installing and configuring RRAS on Windows Server Core to ensure their VPN infrastructure’s best security and performance.

Server Core Benefits

Windows Server Core is a minimal installation option of the Windows Server operating system that provides numerous benefits, particularly for environments where security, resource efficiency, and reduced maintenance overhead are essential. Here are some of the key benefits of using Windows Server Core.

Minimized Attack Surface – Windows Server Core has a smaller footprint compared to the full GUI version, which means fewer components and services are installed by default. This reduces the potential attack surface and minimizes security vulnerabilities.

Enhanced Security – With fewer components and a reduced attack surface, there are fewer potential vectors for malware or unauthorized access. This makes Windows Server Core a more secure choice for critical server roles like RRAS.

Reduced Maintenance – Since there are fewer components to update, patching and maintaining a Windows Server Core system is quicker and requires less effort. This is especially beneficial in large-scale server deployments.

Improved Stability – By removing the graphical user interface (GUI), Windows Server Core has fewer processes running in the background, leading to a more stable and predictable server environment.

Simplified Management – Windows Server Core is designed for remote administration. It allows the administrator to manage it using command-line tools, PowerShell, or remote management tools like the Remote Server Administration Tools (RSAT) and Windows Admin Center. This makes it easier to manage multiple servers from a single location.

Faster Reboots – Windows Servers require periodic reboots. With Windows Server Core, reboot times are considerably faster, resulting in less downtime during maintenance periods.

RSAT

The Remote Server Administration Tools (RSAT) can be installed on Windows clients and servers to enable remote administration using the familiar Routing and Remote Access Management console (rrasmgmt.msc) and Remote Access Management console (ramgmtui.exe) GUI tools.

Windows Client

To install the Remote Access Management tools on Windows client operating systems, navigate to Settings > Apps > Optional Features. Click Add a feature, select RSAT: Remote Access Management Tools, then click Install.

Optionally the Remote Access Management tools can be installed by running the following PowerShell command.

Add-WindowsCapability -Online -Name Rsat.RemoteAccess.Management.Tools~~~~0.0.1.0

Windows Server

To install the Remote Access Management tools on Windows Server run the following PowerShell command.

Install-WindowsFeature -Name RSAT-RemoteAccess

Windows Admin Center

The Windows Admin Center is a free remote management tool from Microsoft for managing Windows Server (core and GUI) remotely. It is especially helpful for Server Core management as it provides a GUI for many common administrative tasks.

You can download Windows Admin Center here.

Additional Information

Windows Server Core Installation Option

Windows Server Core vs. Desktop

PowerShell Remote Server Administration

Windows Admin Center

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

DirectAccess and Windows Server 2012 R2 Core

Important Note: The ability to switch back and forth between the full GUI and core versions of Windows was removed from Windows Server 2016. If you are deploying DirectAccess on Windows Server 2016, you must install server core initially. More details here.

DirectAccess and Windows Server 2012 R2 Core

Windows Server Core is an operating system configuration option that does not include a Graphical User Interface (GUI). Server Core was first introduced with Windows Server 2008 and originally included only a limited number of supported roles. With each subsequent release, Microsoft continues to add support for additional roles on Server Core. Beginning with Windows Server 2012, the Routing and Remote Access (RRAS) role, which includes DirectAccess, is a supported workload on Server Core.

Advantages of Server Core

There are a number of important advantages that come with running DirectAccess on Server Core. Server Core has a greatly reduced attack surface compared to the full GUI version, which is positive from a security perspective. Server Core also features a dramatically reduced footprint, consuming less RAM and disk space. System startup times are faster, and this refactored installation option also reduces servicing requirements (patching), eliminating many reboots and increasing availability and overall system uptime.

DirectAccess and Windows Server 2012 R2 Core

Figure 1 – Windows Server 2012 R2 Core Desktop (Yes, that’s it!)

Server Core Configuration

DirectAccess is a workload that lends itself well to running on Server Core, and I highly recommend leveraging this configuration whenever possible. Based on my experience, I suggest performing initial configuration and testing of the DirectAccess solution with the GUI installed, and then removing the GUI just before placing the DirectAccess server in to production. Removing the GUI can be accomplished by executing the following PowerShell command:

Remove-WindowsFeature Server-Gui-Mgmt-Infra –Restart

Once the server has been converted to Server Core, all administration must be performed at the command line on the server, or remotely from a management server or workstation using the command line or GUI administration tools. You can install the Remote Access Management console on any Windows Server 2012 R2 server using the following PowerShell command:

Install-WindowsFeature RSAT-RemoteAccess

Optionally you can download and install the Windows Server Remote Administrations Tools (RSAT) on a Windows client workstation, if desired.

Minimal Server Interface Configuration

If you prefer to be able to manage the DirectAccess server locally using the GUI, consider enabling the Minimal Server Interface. Minimal Server Interface is a configuration option that lies between Server Core and the full GUI interface. It features some of the benefits of Server Core, while at the same time providing local access to GUI management tools such as the Remote Access Management console. You can configure Minimal Server Interface using the following PowerShell command:

Remove-WindowsFeature Server-Gui-Shell -Restart

You can access the Remote Access Management console by entering RaMgmtUI.exe from the command line.

Revert to Full GUI

If at any point in the future you require the GUI for some reason, re-installing it can be accomplished using the following PowerShell command:

Install-WindowsFeature Server-Gui-Shell –Restart

Summary

With the Unified Remote Access role supported on Windows Server Core, consider implementing DirectAccess using this option to improve the security and increase the availability of your remote access solution. You’ll find that almost all ongoing server maintenance and support can be accomplished remotely using GUI tools, or locally using PowerShell. And if you ever need the GUI again, you can always add it back if necessary!

Additional Resources

DirectAccess on Windows Server 2016 Core