DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Introduction

When preparing a DirectAccess server, an SSL certificate is required for the IP-HTTPS IPv6 transition technology. This certificate is often issued by a public Certification Authority (CA), but it can also be issued an organization’s internal Public Key Infrastructure (PKI).

SSL Certificate

Commonly an SSL certificate is issued for a single hostname, or subject. As long as the hostname matches the subject, everything works fine.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Multi-SAN SSL Certificate

To ease the management burden of using multiple certificates, or reduce the expense associated with using a wildcard certificate, organizations can request a multi-SAN (Subject Alternative Name) certificate, which matches more than one subject. The additional subjects are included in the Subject Alternative Name field on the SSL certificate.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS
A single multi-SAN certificate can be installed on multiple hosts and will work without issue as long as the hostname matches one of the SAN entries.

DirectAccess and Multi-SAN Certificates

When implementing DirectAccess in a multisite configuration, each entry point in the organization will have a unique public hostname. Instinctively, using a multi-SAN SSL certificate in this scenario would seem ideal.

Unfortunately, support for multi-SAN SSL certificates with DirectAccess is limited. To use a multi-SAN certificate for DirectAccess IP-HTTPS, the public hostname must match the name listed in the Subject field. In the example above, the subject is da.richardhicks.net, with SAN entries for da-west.richardhicks.net and da-east.richardhicks.net.

In this scenario, only the public name da.richardhicks.net is supported for use with DirectAccess. It will not work for any of the SAN entries. For example, attempting to configure DirectAccess to use this certificate with the public hostname da-west.richardhicks.net will fail with the following error message.

The subject name of certificate CN=[certificate subject name] is invalid.
Select a certificate with a valid subject name.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Attempting to work around this issue by using the Set-DAServer PowerShell cmdlet also fails to recognize the SSL certificate correctly.

DirectAccess and Multi-SAN SSL Certificates for IP-HTTPS

Summary

Using a multi-SAN SSL certificate for the DirectAccess IP-HTTPS IPv6 transition technology is only supported when the public hostname matches the subject name of the certificate. Configuring DirectAccess with a public hostname listed in the SAN list is not supported. For multisite DirectAccess deployments, individual certificates must be issued for each entry point. Alternatively, a wildcard certificate can be used.

DirectAccess and Windows 10 Better Together

With the release of Windows 10, many organizations who chose to skip Windows 8 are now beginning to deploy this new client operating systemn. To maximize investment in Windows 10, DirectAccess can be leveraged to provide employees with seamless and transparent, always on, secure remote corporate network connectivity. DirectAccess has been around for many years, and today the most popular DirectAccess client is Windows 7. However, Windows 10 provides better support for DirectAccess features that enhance performance and availability, while at the same making it easier to implement and support. Windows 10 opens up many new and compelling deployment scenarios for small businesses to large scale enterprises.

Full Support for Geographic Redundancy

Without a doubt the most important DirectAccess feature Windows 10 supports is automatic entry point selection and transparent failover for multisite deployments. DirectAccess multisite deployment provides essential geographic redundancy for organizations with multiple physical locations. Windows 7 has only minimal support for multisite deployment, with clients required to be assigned to a single entry point. Windows 10 clients are aware of all entry points and will intelligently select the closest entry point when establishing a DirectAccess connection. If the entry point becomes unavailable during the connection, Windows 10 clients will transparently connect to another entry point automatically.

Better Scalability and Performance

Windows 10, like Windows 8 before it, includes support for IP-HTTPS null encryption. This feature greatly improves scalability on the DirectAccess server by eliminating the needless double encryption that Windows 7 clients perform. This reduces resource consumption on the server and enables the server to support many more DirectAccess client connections.

DirectAccess and Windows 10 Better Together

Enhanced Supportability

Many will also appreciate Windows 10’s built-in DirectAccess connectivity status indicator. No longer will administrators have to deploy, manage, and maintain additional software to provide this essential functionality.

To access DirectAccess information in Windows 10, press Window Key + I, click Network & Internet, and then click the DirectAccess tab. Here you will find vital details about DirectAccess configuration and status such as connection state, currently connected entry point, and a site selection drop down box (if manual site selection is enabled by an administrator). In addition you can generate and collect log information for troubleshooting purposes.

DirectAccess and Windows 10 Better Together

Native PowerShell Support

Anyone tasked with troubleshooting DirectAccess configuration and connectivity issues will appreciate the native PowerShell integration with DirectAccess in Windows 10. With just a few commands a wealth of information about DirectAccess configuration and connectivity status can be obtained.

Need to quickly determine if a Windows 10 client has been provisioned for DirectAccess successfully?

Get-DAClientExperienceConfiguration

DirectAccess and Windows 10 Better Together

Has the Windows 10 client connected successfully? If not, why?

Get-DAConnectionStatus

DirectAccess and Windows 10 Better Together

Need to identify the Network Location Server (NLS) the client is configured to use?

Get-NCSIPolicyConfiguration

DirectAccess and Windows 10 Better Together

Looking for DirectAccess multisite entry point details and connection status?

Get-DAEntryPointTableItem

DirectAccess and Windows 10 Better Together

PKI Optional (But Recommended)

Finally, when Windows 10 (and Windows 8.x) clients are supported exclusively a Public Key Infrastructure (PKI) is optional. Here instead the Kerberos Proxy is leveraged to perform DirectAccess client authentication, which reduces infrastructure requirements by eliminating the need for a PKI. However, this configuration offers only limited support for DirectAccess features. For example, a PKI is still required if any Windows 7 clients are deployed. Also, PKI is required to support features such as one-time password (OTP) authentication, Microsoft Network Access Protection (NAP) integration, load balancing (integrated or external), force tunneling, and multisite configuration.

DirectAccess and Windows 10 Better Together

For optimum security and maximum deployment flexibility it is recommended that PKI be used to manage certificates for all DirectAccess deployments including those supporting only Windows 8.x and Windows 10 clients.

Summary

DirectAccess and Windows 10 are much better together. Windows 10 provides full support for the geographic load balancing features of DirectAccess and at the same time offers improved scalability and performance. Windows 10 also makes supporting and troubleshooting DirectAccess clients much easier. And for smaller deployments, Windows 10 can lower the barrier to entry for organizations considering DirectAccess by eliminating the need for a full PKI deployment.

Additional Resources

Video: DirectAccess and Windows 10 in Action
DirectAccess and Windows 10 in Education
Implementing DirectAccess with Windows Server 2016 Book
Implementing DirectAccess with Windows Server 2016 Video Training Course
DirectAccess Consulting Services

More Information

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Overview of New DirectAccess Features in Windows Server 2012

Microsoft recently announced the Release to Manufacturing (RTM) for Windows Server 2012. Windows Server 2012 includes a new Unified Remote Access role that provides many new and exciting features. Along with significant enhancements to DirectAccess, the Routing and Remote Access Service (RRAS) can now be co-located with DirectAccess server to provide legacy remote access VPN client connectivity (PPTP, L2TP/IPsec, and SSTP) as well as site-to-site VPN. Windows Server 2012 can now serve as your consolidated remote access solution and can be managed from a single management console. Here’s an overview of some of the compelling new features found in Windows Server 2012 DirectAccess.

Simplified and Flexible Deployment

Windows Server 2012 DirectAccess includes a new simplified deployment model makes implementing DirectAccess incredibly simple. After adding the Remote Access role, configuring DirectAccess can be done, quite literally, in just three mouse clicks. The new simplified deployment model does have some limitations, so the deployment wizard includes the flexibility to fully customize the implementation according to your specific requirements. Also, DirectAccess in Windows Server 2012 now supports deployment behind an existing edge firewall or border router/NAT device. Previous versions of DirectAccess had a hard requirement to be placed directly on the network edge and have two public IPv4 addresses assigned to it. In addition, Windows Server 2012 DirectAccess now also supports a single network adapter configuration, allowing the remote access gateway to be deployed inside of an existing perimeter network or DMZ. Another significant improvement with DirectAccess in Windows Server 2012 is support for multiple network entry points for DirectAccess clients. This feature is essential for large organizations with a requirement for automatic and transparent redundancy and intelligent client roaming. To simplify deployment and management, PowerShell 3.0 included with Windows Server 2012 can be used to fully automate and manage all aspects of the Unified Remote Access and DirectAccess gateway role. Finally, Windows Server 2012 also supports Offline Domain Join which allows administrators to join computers to the domain without having corporate network connectivity.

Reduced Infrastructure Requirements

A major limitation to DirectAccess in Windows Server 2008 R2 was the requirement for running IPv6 on the internal corporate network. As a workaround, Forefront Unified Access Gateway (UAG) 2010 could be deployed in the DirectAccess gateway role as it included protocol translators (DNS64 and NAT64) which allowed DirectAccess clients to communicate with intranet resources that were running only IPv4. However, deploying Forefront UAG added expense and complexity to the solution. Forefront UAG 2010 is no longer required to support this scenario, as the DNS64 and NAT64 protocol translators are now included in Windows Server 2012 DirectAccess. The new simplified deployment model eliminates the requirement for a Public Key Infrastructure (PKI), although certificates are still required for authentication so self-signed certificates are employed. A PKI is still the recommended and preferred way to implement certificates, and in fact a PKI is a requirement in certain deployment scenarios, such as when forced tunneling is configured, or when strong authentication or Network Access Protection integration is required.

Performance, Scalability and High Availability Improvements

The Microsoft core networking team did a tremendous job addressing the performance and scalability limitations of previous iterations of DirectAccess. A common complaint from those who have deployed earlier versions of DirectAccess was the performance of the IP-HTTPS transition protocol. In a nutshell, a DirectAccess client would fall back to using IP-HTTPS for DirectAccess communication when it was located behind a NAT device that was also preventing outbound UDP 3544. When this occurred, IPsec encrypted tunnels would then be encrypted again with SSL/TLS. This placed heavy demands on both the client and server side of the tunnel and severely reduced performance and limited scalability. In Windows Server 2012 DirectAccess, IP-HTTPS performance is on par with that of Teredo, as IP-HTTPS now uses null encryption for DirectAccess communication, eliminating the redundant and needless double encryption. With the simplified deployment scenario, only a single IPsec tunnel is required for DirectAccess corporate network connectivity. Requiring just one IPsec tunnel for each client reduces the processing load on the DirectAccess gateway significantly in large scale deployments. In terms of reliability, true high availability is now included with DirectAccess in Windows Server 2012 with the inclusion of Network Load Balancing (NLB) support for DirectAccess gateways. NLB provides efficient active/active clustering capabilities that offer more flexible scalability than using failover clustering in previous DirectAccess releases.

Security

DirectAccess in Windows Server 2012 includes additional security options. DirectAccess now natively supports strong authentication using RADIUS One-Time Passwords (OTP), and also supports Virtual Smart Cards hosted on the mobile computer’s Trusted Platform Module (TPM). The Unified Remote Access role can be deployed on Server Core, which substantially improves the overall security of the solution by reducing the attack surface, while at the same time decreasing system downtime by reducing the number of updates required by the operating system. In addition, a new feature of the Windows 8 client prompts the user for network credentials, if necessary, to facilitate remote corporate network connectivity when the DirectAccess client is located behind an authenticating proxy.

As you can see, there are many new and exciting features and capabilities included in the new Unified Remote Access role on Windows Server 2012. Many of these features will greatly simplify the configuration, deployment, and management of remote access and DirectAccess. Also, many of the new capabilities provided with Windows Server 2012 DirectAccess effectively eliminate the need to deploy Forefront Unified Access Gateway (UAG) 2010, making the overall solution less complex and more cost effective. Windows Server 2012 DirectAccess will provide support for Windows 7 Enterprise and Ultimate clients. However, Windows 8 Enterprise clients will be required to take full advantage of many of the new advanced features of Windows Server 2012 DirectAccess.

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