Always On VPN SSL Certificate Requirements for SSTP

Always On VPN Certificate Requirements for SSTPThe Windows Server 2016 Routing and Remote Access Service (RRAS) is commonly deployed as a VPN server for Windows 10 Always On VPN deployments. Using RRAS, Always On VPN administrators can take advantage of Microsoft’s proprietary Secure Socket Tunneling Protocol (SSTP) VPN protocol. SSTP is a Transport Layer Security (TLS) based VPN protocol that uses HTTPS over the standard TCP port 443 to encapsulate and encrypt communication between the Always On VPN client and the RRAS VPN server. SSTP is a firewall-friendly protocol that ensures ubiquitous remote network connectivity. Although IKEv2 is the protocol of choice when the highest level of security is required for VPN connections, SSTP can still provide very good security when implementation best practices are followed.

SSTP Certificate

Since SSTP uses HTTPS for transport, a common SSL certificate must be installed in the Local Computer/Personal/Certificates store on the RRAS VPN server. The certificate must include the Server Authentication Enhanced Key Usage (EKU) at a minimum. Often SSL certificates include both the Server Authentication and Client Authentication EKUs, but the Client Authentication EKU is not strictly required. The subject name on the certificate, or at least one of the Subject Alternative Name entries, must match the public hostname used by VPN clients to connect to the VPN server. Multi-SAN (sometimes referred to as UC certificates) and wildcard certificates are supported.

Always On VPN Certificate Requirements for SSTP

Certification Authority

It is recommended that the SSL certificate used for SSTP be issued by a public Certification Authority (CA). Public CAs typically have their Certificate Revocation Lists (CRLs) hosted on robust, highly available infrastructure. This reduces the chance of failed VPN connection attempts caused by the CRL being offline or unreachable.

Using an SSL certificate issued by an internal, private CA is supported if the CRL for the internal PKI is publicly available.

Key Type

RSA is the most common key type used for SSL certificates. However, Elliptic Curve Cryptography (ECC) keys offer better security and performance, so it is recommended that the SSTP SSL certificate be created using an ECC key instead.

Always On VPN Certificate Requirements for SSTP

To use an ECC key, be sure to specify the use of a Cryptographic Next Generation (CNG) key and select the ECDSA_P256 Microsoft Software Key Storage Provider (CSP) (or greater) when creating the Certificate Signing Request (CSR) for the SSTP SSL certificate.

Always On VPN Certificate Requirements for SSTP

Most public CAs will support certificate signing using ECC and Elliptic Curve Digital Signature Algorithm (ECDSA). If yours does not, find a better CA. 😉

Forward Secrecy

Forward secrecy (sometimes referred to as perfect forward secrecy, or PFS) ensures that session keys can’t be compromised even if the server’s private key is compromised. Using forward secrecy for SSTP is crucial to ensuring the highest levels of security for VPN connections.

To enforce the use of forward secrecy, the TLS configuration on the VPN server should be prioritized to prefer cipher suites with Elliptic Curve Diffie-Hellman Ephemeral (ECDHE) key exchange.

Authenticated Encryption

Authenticated encryption (AE) and authenticated encryption with associated data (AEAD) is a form of encryption that provides better data protection and integrity compared to older block or stream ciphers such as CBC or RC4.

To enforce the use of authenticated encryption, the TLS configuration on the VPN server should be prioritized to prefer cipher suites that support Galois/Counter Mode (GCM) block ciphers.

Important Note: In Windows Server 2016, GCM ciphers can be used with both RSA and ECC certificates. However, in Windows Server 2012 R2 GCM ciphers can only be used when an ECC certificate is used.

SSL Offload

Offloading SSL to a load balancer or application delivery controller (ADC) can be enabled to improve scalability and performance for SSTP VPN connections. I will cover SSL offload for SSTP in detail in a future post.

Summary

SSTP can provide good security for VPN connections when implementation and security best practices are followed. For optimum security, use an SSL certificate with an EC key and optimize the TLS configuration to use forward secrecy and authenticated cipher suites.

Additional Information

Always On VPN and Windows Server Routing and Remote Access Service (RRAS)

Always On VPN Protocol Recommendations for Windows Server RRAS

Always On VPN Certificate Requirements for IKEv2

3 Important Advantages of Always On VPN over DirectAccess

Microsoft SSTP Specification on MSDN

Comparing DirectAccess and NetMotion Mobility

Comparing DirectAccess and NetMotion Mobility With DirectAccess approaching the end of its useful lifetime, many organizations are considering alternative solutions to provide seamless, transparent, always on remote connectivity for their field-based workers. Microsoft is positioning Windows 10 Always On VPN as the replacement for DirectAccess. While it provides many new features that were missing from DirectAccess, it has its own unique limitations and shortcomings.

NetMotion Mobility

Comparing DirectAccess and NetMotion Mobility NetMotion Mobility is an excellent alternative to DirectAccess and Always On VPN, and it has many advantages over both native Microsoft offerings. NetMotion Mobility offers better security and performance. It provides deep visibility with broad client support, and the solution is easier to support than DirectAccess.

Comparing DirectAccess and NetMotion Mobility

If you’d like to learn more about how NetMotion Mobility compares with DirectAccess, you will find detailed comparison information in my Comparing NetMotion Mobility and DirectAccess article series on the NetMotion blog.

Comparing NetMotion Mobility and DirectAccess – Security
Comparing NetMotion Mobility and DirectAccess – Performance
Comparing NetMotion Mobility and DirectAccess – Visibility
Comparing NetMotion Mobility and DirectAccess – Supported Clients
Comparing NetMotion Mobility and DirectAccess – Support

NetMotion Mobility in Action

Watch the following videos to see NetMotion Mobility in action.

NetMotion Mobility Demonstration Video
NetMotion Mobility and Skype for Business Demonstration Video

DirectAccess Alternative

NetMotion Mobility is a premium remote access solution with many of the same characteristics as DirectAccess; seamless, transparent, and always on. It is feature rich with numerous compelling benefits over native Microsoft remote access technologies. Organizations seeking a solution to replace Microsoft DirectAccess would benefit greatly from NetMotion Mobility.

Learn More

If you’d like to learn more about NetMotion Mobility, or if you’d like to evaluate their solution, fill out the form below and I’ll respond with more information.

DirectAccess Selective Tunneling

DirectAccess Selective TunnelingDirectAccess administrators, and network administrators in general, are likely familiar with the terms “split tunneling” and “force tunneling”. They dictate how traffic is handled when a DirectAccess (or VPN) connection is established by a client. Split tunneling routes only traffic destined for the internal network over the DirectAccess connection; all other traffic is routed directly over the Internet. Force tunneling routes all traffic over the DirectAccess connection.

Force Tunneling

DirectAccess uses split tunneling by default. Optionally, it can be configured to use force tunneling if required. Force tunneling is commonly enabled when DirectAccess administrators want to inspect and monitor Internet traffic from field-based clients.

Note: One-time password user authentication is not supported when force tunneling is enabled. Details here.

Drawbacks

Force tunneling is not without its drawbacks. It requires that an on-premises proxy server be used by DirectAccess clients to access the Internet, in most cases. In addition, the user experience is often poor when force tunneling is enabled. This is caused by routing Internet traffic, which is commonly encrypted, over an already encrypted connection. The added protocol overhead caused by double encryption (triple encryption if you are using Windows 7!) along with using a sub-optimal network path increases latency and can degrade performance significantly. Also, location-based services typically fail to work correctly.

Selective Tunneling

“Selective Tunneling” is a term that I commonly use to describe a configuration where only one or a few specific public resources are tunneled over the DirectAccess connection. A common use case is where access to a cloud-based application is restricted to the IP address of a corporate proxy or firewall.

Using the Name Resolution Policy Table (NRPT) and taking advantage of DirectAccess and its requirement for IPv6, DirectAccess administrators can choose to selectively route requests for public hosts or domains over the DirectAccess connection. The process involves defining the public Fully Qualified Domain Name (FQDN) as “internal” in the DirectAccess configuration and then assigning an on-premises proxy server for DirectAccess clients to use to access that namespace.

Enable Selective Tunneling

While some of the selective tunneling configuration can be performed using the Remote Access Management console, some of it can only be done using PowerShell. For this reason, I prefer to do everything in PowerShell to streamline the process.

Run the following PowerShell commands on the DirectAccess server to enable selective tunneling for the “.example.com” domain.

$namespace = “.example.com” # include preceding dot for namespace, omit for individual host
$dnsserver = Get-ItemPropertyValue –Path HKLM:\\SYSTEM\CurrentControlSet\Services\RaMgmtSvc\Config\Parameters -Name DnsServers

Add-DAClientDnsConfiguration -DnsSuffix $namespace -DnsIpAddress $dnsserver -PassThru

$gpo = (Get-RemoteAccess).ClientGpoName
$gpo = $gpo.Split(‘\’)[1]
$proxy = “proxy.corp.example.net:8080” # this is the FQDN and port for the internal proxy server
$rule = (Get-DnsClientNrptRule -GpoName $gpo | Where-Object Namespace -eq $namespace | Select-Object -ExpandProperty “Name”)

Set-DnsClientNrptRule -DAEnable $true -DAProxyServerName $proxy -DAProxyType “UseProxyName” -Name $rule -GpoName $gpo

If Windows 7 client support has been enabled, run the following PowerShell commands on the DirectAccess server. If multisite is enabled, run these commands on one DirectAccess server in each entry point.

$downlevelgpo = (Get-RemoteAccess).DownlevelGpoName
$downlevelgpo = $downlevelgpo.Split(‘\’)[1]
$proxy = “proxy.corp.example.net:8080” # this is the FQDN and port for the internal proxy server
$downlevelrule = (Get-DnsClientNrptRule -GpoName $downlevelgpo | Where-Object Namespace -eq $namespace | Select-Object -ExpandProperty “Name”)

Set-DnsClientNrptRule -DAEnable $true -DAProxyServerName $proxy -DAProxyType “UseProxyName” -Name $downlevelrule -GpoName $downlevelgpo

To remove a namespace from the NRPT, run the following PowerShell command.

Remove-DAClientDnsConfiguration -DnsSuffix $namespace

Caveats

While selective tunneling works well for the most part, the real drawback is that only Microsoft browsers (Internet Explorer and Edge) are supported. Web sites configured for selective tunneling will not be reachable when using Chrome, Firefox, or any other third-party web browser. In addition, many web sites deliver content using more than one FQDN, which may cause some web pages to load improperly.

Additional Resources

DirectAccess Force Tunneling and Proxy Server Configuration

NetMotion Mobility for DirectAccess Administrators – Split vs. Force Tunneling

Deleting an Always On VPN Device Tunnel

Deleting an Always On VPN Device TunnelWindows 10 Always On VPN supports both a user tunnel for corporate network access, and a device tunnel typically used to provide pre-logon network connectivity and to support manage out scenarios. The process of testing Always On VPN is often an iterative one involving trial and error testing to fine tune the configuration parameters to achieve the best experience. As a part of this process it will often be necessary to delete a connection at some point. For the user tunnel the process is simple and straightforward. Simply disconnect the session and delete the connection in the UI.

Deleting an Always On VPN Device Tunnel

Deleting a device tunnel connection presents a unique challenge though. Specifically, there is no VPN connection in the UI to disconnect and remove. To delete an Always On VPN device tunnel, open an elevated PowerShell window and enter the following command.

Get-VpnConnection -AllUserConnection | Remove-VpnConnection -Force

If the device tunnel is connected when you try to remove it, you will receive the following error message.

The VPN connection [connection_name] cannot be removed from the global user connections. Cannot
delete a connection while it is connected.

Deleting an Always On VPN Device Tunnel

The device tunnel must first be disconnected to resolve this issue. Enter the following command to disconnect the device tunnel.

rasdial.exe [connection_name] /disconnect

Remove the device tunnel connection using PowerShell once complete.

Deleting an Always On VPN Device Tunnel
Additional Resources

Windows 10 Always On VPN Device Tunnel Step-by-Step Configuration using PowerShell

What’s The Difference Between DirectAccess and Always On VPN?

Windows 10 Always On VPN Recommendations for Windows Server 2016 Routing and Remote Access Service (RRAS)

Windows 10 Always On VPN Hands-On Training

What is the Difference Between DirectAccess and Always On VPN?

Always On VPN Device Tunnel Configuration Guidance Now AvailableDirectAccess has been around for many years, and with Microsoft now moving in the direction of Always On VPN, I’m often asked “What’s the difference between DirectAccess and Always On VPN?” Fundamentally they both provide seamless and transparent, always on remote access. However, Always On VPN has a number of advantages over DirectAccess in terms of security, authentication and management, performance, and supportability.

Security

DirectAccess provides full network connectivity when a client is connected remotely. It lacks any native features to control access on a granular basis. It is possible to restrict access to internal resources by placing a firewall between the DirectAccess server and the LAN, but the policy would apply to all connected clients.

Windows 10 Always On VPN includes support for granular traffic filtering. Where DirectAccess provides access to all internal resources when connected, Always On VPN allows administrators to restrict client access to internal resources in a variety of ways. In addition, traffic filter policies can be applied on a per-user or group basis. For example, users in accounting can be granted access only to their department servers. The same could be done for HR, finance, IT, and others.

Authentication and Management

DirectAccess includes support for strong user authentication with smart cards and one-time password (OTP) solutions. However, there is no provision to grant access based on device configuration or health, as that feature was removed in Windows Server 2016 and Windows 10. In addition, DirectAccess requires that clients and servers be joined to a domain, as all configuration settings are managed using Active Directory group policy.

Windows 10 Always On VPN includes support for modern authentication and management, which results in better overall security. Always On VPN clients can be joined to an Azure Active Directory and conditional access can also be enabled. Modern authentication support using Azure MFA and Windows Hello for Business is also supported. Always On VPN is managed using Mobile Device Management (MDM) solutions such as Microsoft Intune.

Performance

DirectAccess uses IPsec with IPv6, which must be encapsulated in TLS to be routed over the public IPv4 Internet. IPv6 traffic is then translated to IPv4 on the DirectAccess server. DirectAccess performance is often acceptable when clients have reliable, high quality Internet connections. However, if connection quality is fair to poor, the high protocol overhead of DirectAccess with its multiple layers of encapsulation and translation often yields poor performance.

The protocol of choice for Windows 10 Always On VPN deployments is IKEv2. It offers the best security and performance when compared to TLS-based protocols. In addition, Always On VPN does not rely exclusively on IPv6 as DirectAccess does. This reduces the many layers of encapsulation and eliminates the need for complex IPv6 transition and translation technologies, further improving performance over DirectAccess.

Supportability

DirectAccess is a Microsoft-proprietary solution that must be deployed using Windows Server and Active Directory. It also requires a Network Location Server (NLS) for clients to determine if they are inside or outside the network. NLS availability is crucial and ensuring that it is always reachable by internal clients can pose challenges, especially in very large organizations.

Windows 10 Always On VPN supporting infrastructure is much less complex than DirectAccess. There’s no requirement for a NLS, which means fewer servers to provision, manage, and monitor. In addition, Always On VPN is completely infrastructure independent and can be deployed using third-party VPN servers such as Cisco, Checkpoint, SonicWALL, Palo Alto, and more.

Summary

Windows 10 Always On VPN is the way of the future. It provides better overall security than DirectAccess, it performs better, and it is easier to manage and support.

Here’s a quick summary of some important aspects of VPN, DirectAccess, and Windows 10 Always On VPN.

Traditional VPN DirectAccess Always On VPN
Seamless and Transparent No Yes Yes
Automatic Connection Options None Always on Always on, app triggered
Protocol Support IPv4 and IPv6 IPv6 Only IPv4 and IPv6
Traffic Filtering No No Yes
Azure AD Integration No No Yes
Modern Management Yes No (group policy only) Yes (MDM)
Clients must be domain-joined? No Yes No
Requires Microsoft Infrastructure No Yes No
Supports Windows 7 Yes Yes Windows 10 only

Always On VPN Hands-On Training

If you are interested in learning more about Windows 10 Always On VPN, consider registering for one of my hands-on training classes. More details here.

Additional Resources

Always On VPN and the Future of Microsoft DirectAccess

5 Important Things DirectAccess Administrators Should Know about Windows 10 Always On VPN

3 Important Advantages of Windows 10 Always On VPN over DirectAccess

Always On VPN Hands-On Training Coming to Chicago

Windows 10 Always On VPN Hands-On Training Classes for 2018Recently I announced the availability of Windows 10 Always On VPN hands-on training classes. The first class is set for March 27-29 in Los Angeles. By popular demand, I’m pleased to announce that I’ll be delivering another class April 10-12 in Chicago. This training class will cover all aspects of designing, implement, and supporting an Always On VPN solution in the enterprise. These three-day courses will cover topics including…

  • Windows 10 Always On VPN overview
  • Introduction to CSP
  • Infrastructure requirements
  • Planning and design considerations
  • Installation, configuration, and client provisioning

Advanced topics will include…

  • Redundancy and high availability+
  • Cloud-based deployments
  • Third-party VPN infrastructure and client support
  • Multifactor authentication
  • Always On VPN migration strategies

Windows 10 Always On VPN Hands-On Training Classes for 2018

Register Today

Reservations are being accepted now! The cost for this 3-day hands-on training class is $4995.00 USD. Space is limited, so don’t wait to register! Fill out the form below to save your seat now.

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShellWindows 10 Always On VPN and DirectAccess both provide seamless, transparent, always on remote network access for Windows clients. However, Always On VPN is provisioned to the user, not the machine as it is with DirectAccess. This presents a challenge for deployment scenarios that require the VPN connection to be established before the user logs on. To address this issue, Microsoft introduced support for a device tunnel configuration option beginning with Windows 10 version 1709 (Fall creators update).

Want to learn more about Windows 10 Always On VPN? Register for one of my hands-on training classes now forming in cities across the U.S. Details here.

Prerequisites

To support an Always On VPN device tunnel, the client computer must be running Windows 10 Enterprise or Education version 1709 (Fall creators update). It must also be domain-joined and have a computer certificate with the Client Authentication Enhanced Key Usage (EKU) issued by the organization’s Public Key Infrastructure (PKI).

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

In addition, only the built-in Windows VPN client is supported for Always On VPN device tunnel. Although Windows 10 Always On VPN user connections can be configured using various third-party VPN clients, they are not supported for use with the device tunnel.

VPN ProfileXML

The Always On VPN device tunnel is provisioned using an XML file. You can download a sample VPN ProfileXML file here. Make any changes required for your environment such as VPN server hostnames, routes, traffic filters, and remote address ranges. Optionally include the trusted network detection code, if required. Do not change the protocol type or authentication methods, as these are required.

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Reference: https://docs.microsoft.com/en-us/windows-server/remote/remote-access/vpn/vpn-device-tunnel-config#configure-the-vpn-device-tunnel

Once the ProfileXML file is created, it can be deployed using Intune, System Center Configuration Manager (SCCM), or PowerShell. In this post I’ll cover how to configure Windows 10 Always On VPN device tunnel using PowerShell.

Client Configuration

Download the PowerShell script located here and then copy it to the target client computer. The Always On VPN device tunnel must be configured in the context of the local system account. To accomplish this, it will be necessary to use PsExec, one of the PsTools included in the Sysinternals suite of utilities. Download PsExec here, copy it to the target machine, and then run the following command in an elevated PowerShell command window.

PsExec.exe -i -s C:\windows\system32\WindowsPowerShell\v1.0\powershell.exe

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Another elevated PowerShell window will open, this one now running in the context of the local system account. In this window, navigate to the folder where you copied the PowerShell script and XML file to. Run the PowerShell script and specify the name of the ProfileXML file, as shown below.

VPN_Profile_Device.ps1 -xmlFilePath .\profileXML_device.XML -ProfileName DeviceTunnel

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

To verify creation of the VPN device tunnel, run the following PowerShell command.

Get-VpnConnection -AllUserConnection

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Note: Be advised that the ConnectionStatus is always Disconnected. Hopefully this will be addressed by Microsoft in the near future.

Server Configuration

If you are using Windows Server 2012 R2 or Windows Server 2016 Routing and Remote Access Service (RRAS) as your VPN server, you must enable machine certificate authentication for VPN connections and define a root certification authority for which incoming VPN connections will be authenticated with. To do this, open an elevated PowerShell command and run the following commands.

$VPNRootCertAuthority = “Common Name of trusted root certification authority”
$RootCACert = (Get-ChildItem -Path cert:LocalMachine\root | Where-Object {$_.Subject -Like “*$VPNRootCertAuthority*” })
Set-VpnAuthProtocol -UserAuthProtocolAccepted Certificate, EAP -RootCertificateNameToAccept $RootCACert -PassThru

Always On VPN Windows 10 Device Tunnel Step-by-Step Configuration using PowerShell

Summary

Once the Always On VPN device tunnel is configured, the client computer will automatically establish the connection as soon as an active Internet connection is detected. This will enable remote logins for users without cached credentials, and allow administrators to remotely manage Always On VPN clients without requiring a user to be logged on at the time.

Additional Information

Configure Windows 10 VPN Device Tunnel on Microsoft.com

3 Important Advantages of Always On VPN over DirectAccess

5 Things DirectAccess Administrators Should Know About Always On VPN 

Windows 10 Always On VPN and the Future of DirectAccess

Windows 10 Always On VPN Training and Consulting Services

5 Things DirectAccess Administrators Should Know About Always On VPN

5 Things DirectAccess Administrators Should Know About Always On VPNWindows 10 Always On VPN hands-on training classes now forming. Details here.

As I’ve written about previously, Microsoft is no longer investing in DirectAccess going forward. There will be no new features or functionality added to the product in the future. Microsoft is now investing in Always On VPN in Windows 10, with new features being released with each semi-annual update of the operating system. But as Microsoft continues to make the push toward Always On VPN over DirectAccess, many administrators have asked about the ramifications of this shift in focus for enterprise remote access. Here are a few points to consider.

It’s the same thing, only different.

Always On VPN provides the same seamless, transparent, always on experience as DirectAccess. Under the covers, the mechanics of how that’s accomplished changes a bit, but fundamentally the user experience is exactly the same. Once a user logs on to their device, a VPN connection is established automatically and the user will have secure remote access to corporate resources.

The connection is still secure.

Where DirectAccess uses IPsec and Connection Security Rules (CSRs) to establish its secure tunnels, Always On VPN uses traditional client-based VPN protocols such as IKEv2, SSTP, L2TP, and PPTP. Both DirectAccess and Always On VPN use certificates for authentication. However, where DirectAccess uses machine certificates to authenticate the computer, Always On VPN leverages user certificates to authenticate the user.

(Note: Machine certificates will be required for Always On VPN when using the optional device tunnel configuration. I will publish more details about this configuration option in a future article.)

Provisioning and managing clients is different.

The administrative experience for Always On VPN is much different than it is with DirectAccess. Where DirectAccess made use of Active Directory and group policy for managing client and server settings, Always On VPN clients must be provisioned using a Mobile Device Management (MDM) solution such as Microsoft Intune, or any third-party MDM platform. Optionally, Always On VPN clients can be provisioned using Microsoft System Center Configuration Manager (SCCM), or manually using PowerShell.

Security is enhanced.

Always On VPN has the potential to provide much more security and protection than DirectAccess. Always On VPN supports traffic filtering, allowing administrators to restrict remote client communication by IP address, protocol, port, or application. By contrast, DirectAccess allows full access to the internal network after user logon with no native capability to restrict access. In addition, Always On VPN supports integration with Azure Active Directory, which enables conditional access and multifactor authentication scenarios.

It’s built for the future.

Always On VPN also provides support for modern authentication mechanisms like Windows Hello for Business. In addition, Windows Information Protection (WIP) integration is supported to provide essential protection for enterprise data.

Summary

Microsoft set the bar pretty high with DirectAccess. Users love the seamless and transparent access it provides, and administrators reap the benefit of improved systems management for field based devices. Always On VPN provides those same benefits, with additional improvements in security and protection. If you’d like more information about Always On VPN, fill out the form below and I’ll get in touch with you.

Additional Information

Always On VPN and the Future of DirectAccess

3 Important Advantages of Windows 10 Always On VPN over Microsoft DirectAccess

Windows 10 Always On VPN Hands-On Training

Always On VPN and the Future of Microsoft DirectAccess

Windows 10 Always On VPN hands-on training classes now forming. Details here.

Since the introduction of Windows Server 2012 in September of 2012, no new features or functionality have been added to DirectAccess. In Windows Server 2016, the only real change aside from bug fixes for DirectAccess is the removal of Network Access Protection (NAP) integration support.

Always On VPN and the Future of Microsoft DirectAccessFigure 1. Remote Access Setup wizard with NAP integration option in Windows Server 2012/R2.

Always On VPN and the Future of Microsoft DirectAccess

Figure 2. Remote Access Setup wizard without NAP integration option in Windows Server 2016.

DirectAccess Roadmap

It’s clear to see that Microsoft is no longer investing in DirectAccess, and in fact their field sales teams have been communicating this to customers for quite some time now. Microsoft has been actively encouraging organizations who are considering a DirectAccess solution to instead implement client-based VPN with Windows 10.

Always On VPN

New features introduced in the Windows 10 Anniversary Update allow IT administrators to configure automatic VPN connection profiles. This Always On VPN connection provides a DirectAccess-like experience using traditional remote access VPN protocols such as IKEv2, SSTP, and L2TP/IPsec. It comes with some additional benefits as well.

  • Conditional access and device compliance with system health checks
  • Windows Hello for Business and Azure multifactor authentication
  • Windows Information Protection (WIP) integration
  • Traffic filters to restrict VPN network access
  • Application-trigger VPN connections

DirectAccess Deprecated?

There has been rampant speculation that Microsoft plans to deprecate and retire DirectAccess. While that may in fact be true, Microsoft has yet to make a formal end-of-life announcement. There’s no reason DirectAccess and VPN couldn’t co-exist, so it’s not a certainty Microsoft will do this. However, there’s also no need to have multiple remote access solutions, and it is abundantly clear that the future for Microsoft remote access is Always On VPN and not DirectAccess.

Always On VPN and the Future of Microsoft DirectAccess

Source: https://social.technet.microsoft.com/wiki/contents/articles/38546.new-features-for-vpn-in-windows-10-and-windows-server-2016.aspx#Advanced_VPN_Connectivity

Always On VPN Advantages and Disadvantages

Windows 10 Always On VPN has some important advantages over DirectAccess. It has some crucial limitations as well.

Advantages

  • Always On VPN supports non-Enterprise Windows 10 client SKUs (Windows 10 Home and Professional)
  • Always On VPN includes support for granular network access control
  • Always On VPN can use both IPv4 and IPv6
  • Always On VPN is infrastructure independent. In addition to supporting Windows RRAS, any third-party network device can be used such as Cisco, Checkpoint, Juniper, Palo Alto, SonicWALL, Fortinet, Sophos, and many more

Disadvantages

  • Always On VPN works only with Windows 10. It is not supported for Windows 7
  • Always On VPN cannot be managed natively using Active Directory and group policy. It must be configured and managed using Microsoft System Center Configuration Manager (SCCM), Microsoft Intune, or PowerShell

DirectAccess or Always On VPN?

Should you deploy DirectAccess today or implement Always On VPN with Windows 10 instead? That depends on a number of factors. It’s important to understand that DirectAccess is fully supported in Windows Server 2016 and will likely be for many years to come. If DirectAccess meets your needs today, you can deploy it with confidence that it will still have a long support life. If you have reservations about the future viability of DirectAccess, and if you meet all of the requirements to support Always On VPN with Windows 10, then perhaps that’s a better choice. If you’d like to discuss your remote access options in more detail, fill out the form below and I’ll get in touch with you.

Additional Resources

5 Things DirectAccess Administrators Should Know About Always On VPN

3 Important Advantages of Always On VPN over DirectAccess

NetMotion Mobility as an Alternative to DirectAccess

Windows 10 Always On VPN Hands-On Training Classes

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

Organizations are rapidly deploying Windows server infrastructure with public cloud providers such as Amazon Web Services (AWS) and Microsoft Azure. With traditional on-premises infrastructure now hosted in the cloud, DirectAccess is also being deployed there more commonly.

Supportability

Interestingly, Microsoft has expressly stated that DirectAccess is not formally supported on their own public cloud platform, Azure. However, there is no formal statement of non-support for DirectAccess hosted on other non-Microsoft public cloud platforms. With supportability for DirectAccess on AWS unclear, many companies are taking the approach that if it isn’t unsupported, then it must be supported. I’d suggest proceeding with caution, as Microsoft could issue formal guidance to the contrary in the future.

DirectAccess on AWS

Deploying DirectAccess on AWS is similar to deploying on premises, with a few notable exceptions, outlined below.

IP Addressing

It is recommended that an IP address be exclusively assigned to the DirectAccess server in AWS, as shown here.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

Prerequisites Check

When first configuring DirectAccess, the administrator will encounter the following warning message.

“The server does not comply with some DirectAccess prerequisites. Resolve all issues before proceed with DirectAccess deployment.”

The warning message itself states that “One or more network adapters should be configured with a static IP address. Obtain a static address and assign it to the adapter.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

IP addressing for virtual machines are managed entirely by AWS. This means the DirectAccess server will have a DHCP-assigned address, even when an IP address is specified in AWS. Assigning static IP addresses in the guest virtual machine itself is also not supported. However, this warning message can safely be ignored.

No Support for Load Balancing

It is not possible to create load-balanced clusters of DirectAccess servers for redundancy or scalability on AWS. This is because enabling load balancing for DirectAccess requires the IP address of the DirectAccess server be changed in the operating system, which is not supported on AWS. To eliminate single points of failure in the DirectAccess architecture or to add additional capacity, multisite must be enabled. Each additional DirectAccess server must be provisioned as an individual entry point.

Network Topology

DirectAccess servers on AWS can be provisioned with one or two network interfaces. Using two network interfaces is recommended, with the external network interface of the DirectAccess server residing in a dedicated perimeter/DMZ network. The external network interface must use either the Public or Private Windows firewall profile. DirectAccess will not work if the external interface uses the Domain profile. For the Public and Private profile to be enabled, domain controllers must not be reachable from the perimeter/DMZ network. Ensure the perimeter/DMZ network cannot access the internal network by restricting network access in EC2 using a Security Group, or on the VPC using a Network Access Control List (ACL) or custom route table settings.

External Connectivity

A public IPv4 address must be associated with the DirectAccess server in AWS. There are several ways to accomplish this. The simplest way is to assign a public IPv4 address to the virtual machine (VM). However, a public IP address can only be assigned to the VM when it is deployed initially and cannot be added later. Alternatively, an Elastic IP can be provisioned and assigned to the DirectAccess server at any time.

An ACL must also be configured for the public IP that restricts access from the Internet to only inbound TCP port 443. To provide additional protection, consider deploying an Application Delivery Controller (ADC) appliance like the Citrix NetScaler or F5 BIG-IP to enforce client certificate authentication for DirectAccess clients.

Network Location Server (NLS)

If an organization is hosting all of its Windows infrastructure in AWS and all clients will be remote, Network Location Server (NLS) availability becomes much less critical than with traditional on-premises deployments. For cloud-only deployments, hosting the NLS on the DirectAccess server is a viable option. It eliminates the need for dedicated NLS, reducing costs and administrative overhead. If multisite is configured, ensure that the NLS is not using a self-signed certificate, as this is unsupported.

Deployment Considerations for DirectAccess on Amazon Web Services (AWS)

However, for hybrid cloud deployments where on-premises DirectAccess clients share the same internal network with cloud-hosted DirectAccess servers, it is recommended that the NLS be deployed on dedicated, highly available servers following the guidance outlined here and here.

Client Provisioning

All supported DirectAccess clients will work with DirectAccess on AWS. If the domain infrastructure is hosted exclusively in AWS, provisioning clients can be performed using Offline Domain Join (ODJ). Provisioning DirectAccess clients using ODJ is only supported in Windows 8.x/10. Windows 7 clients cannot be provisioned using ODJ and must be joined to the domain using another form of remote network connectivity such as VPN.

Additional Resources

DirectAccess No Longer Supported in Microsoft Azure

Microsoft Server Software Support for Azure Virtual Machines

DirectAccess Network Location Server (NLS) Guidance

DirectAccess Network Location Server (NLS) Deployment Considerations for Large Enterprises

Provisioning DirectAccess Clients using Offline Domain Join (ODJ)

DirectAccess SSL Offload and IP-HTTPS Preauthentication with Citrix NetScaler

DirectAccess SSL Offload and IP-HTTPS Preauthentication with F5 BIG-IP

Planning and Implementing DirectAccess with Windows Server 2016 Video Training Course

Implementing DirectAccess with Windows Server 2016 Book

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