Windows Server 2012 and 2012 R2 End of Life

DirectAccess on Microsoft Windows

I want to remind you of a critical upcoming milestone that may affect your business. In just 60 days, we will reach the end of support for Windows Server 2012 and Windows Server 2012 R2. As of October 10, 2023, these operating systems will no longer receive security updates or technical support from Microsoft.

End of Support

End of support means your servers will be more vulnerable to security risks and potential threats. It is essential to take action now to ensure your IT infrastructure’s continued security and stability. Upgrading to newer, supported operating systems will protect your data and systems from potential cyber threats and provide access to enhanced features and performance improvements.

Don’t Wait

Now is the time to migrate those remaining workloads for those still running Windows Server 2012 and 2012 R2! Consider the following commonly deployed services that may still be running on Windows Server 2012 or 2012 R2 in your organization.

Remote Access – Windows Server Routing and Remote Access Service (RRAS) is commonly deployed to provide secure remote access for field-based workers. In addition, Absolute Secure Access (formerly NetMotion Mobility) is a widely implemented premium alternative to RRAS. Organizations may be hesitant to migrate these workloads because disrupting remote workers is painful.

DirectAccess – This remote access technology is widely deployed and extremely difficult to migrate. In addition, the complex nature of DirectAccess, with its many intricate interdependencies, poses a significant challenge to organizations migrating this role.

PKI – This is likely the most common enterprise service to be found running on Windows Server 2012 and 2012R2. Most organizations relying on Windows Active Directory Certificate Services (AD CS) to issue and manage enterprise certificates are reluctant to move this workload once it is deployed. This service is much easier to migrate than you might think! It can be done without disruption as well.

Consulting Services

We understand that upgrading might require careful planning and coordination, and our team is here to support you throughout the transition process. Don’t delay – take this opportunity to safeguard your organization’s data and systems by upgrading to the latest Windows Server version or exploring cloud-based solutions.

Get In Touch

Please don’t hesitate to contact us for further assistance or any questions regarding the upgrade process. Together, let’s ensure your business remains secure and productive. You can get started today by booking a free one-hour consultation to discuss your migration strategy. Just fill out the form below and I’ll provide more information.

Enterprise Networking Magazine Top 10 VPN Consulting Services 2020

It is with great pleasure that I announce Richard M. Hicks Consulting, Inc. has been included in Enterprise Networking Magazine’s Top 10 VPN consulting services for 2020! Enterprise Networking Magazine is a leading magazine and web site dedicated to the enterprise networking industry and its professionals.

Enterprise Networking Magazine Top 10 VPN Consulting Services 2020

You can read the full write-up on Richard M. Hicks Consulting, Inc. at Enterprise Networking’s web site here.

DirectAccess Manage Out and System Center Configuration Manager (SCCM)

The seamless and transparent nature of DirectAccess makes it wonderfully easy to use. In most cases, it requires no user interaction at all to access internal corporate resources while away from the office. This enables users to be more productive. At the same time, it offers important connectivity benefits for IT administrators and systems management engineers as well.

Always Managed

DirectAccess Manage Out and System Center Configuration Manager (SCCM)DirectAccess clients are automatically connected to the corporate network any time they have a working Internet connection. Having consistent corporate network connectivity means they receive Active Directory group policy updates on a regular basis, just as on-premises systems do. Importantly, they check in with internal management systems such as System Center Configuration Manager (SCCM) and Windows Server Update Services (WSUS) servers, enabling them to receive updates in a timely manner. Thus, DirectAccess clients are better managed, allowing administrators to more effectively maintain the configuration state and security posture for all their managed systems, including those that are predominantly field-based. This is especially crucial considering the prevalence WannaCry, Cryptolocker, and a variety of other types of ransomware.

DirectAccess Manage Out

DirectAccess Manage Out and System Center Configuration Manager (SCCM)When manage out is configured with DirectAccess, hosts on the internal network can initiate connections outbound to remote connected DirectAccess clients. SCCM Remote Control and Remote Desktop Connection (RDC) are commonly used to remotely connect to systems for troubleshooting and support. With DirectAccess manage out enabled, these and other popular administrative tools such as VNC, Windows Remote Assistance, and PowerShell remoting can also be used to manage remote DirectAccess clients in the field. In addition, enabling manage out allows for the proactive installation of agents and other software on remote clients, such as the SCCM and System Center Operation Manager (SCOM) agents, third-party management agents, antivirus and antimalware software, and more. A user does not have to be logged on to their machine for manage out to work.

IPv6

DirectAccess manage out requires that connections initiated by machines on the internal network to remote-connected DirectAccess clients must be made using IPv6. This is because DirectAccess clients use IPv6 exclusively to connect to the DirectAccess server. To enable connectivity over the public IPv4 Internet, clients use IPv6 transition technologies (6to4, Teredo, IP-HTTPS), and IPv6 translation components on the server (DNS64 and NAT64) enable clients to communicate with internal IPv4 resources. However, DNS64 and NAT64 only translate IPv6 to IPv4 inbound. They do not work in reverse.

Native or Transition?

It is recommended that IPv6 be deployed on the internal network to enable DirectAccess manage out. This is not a trivial task, and many organizations can’t justify the deployment for just this one specific use case. As an alternative, IPv6 can be configured with an IPv6 transition technology, specifically the Intrasite Automatic Tunnel Addressing Protocol (ISATAP). ISATAP functions as an IPv6 overlay network, allowing internal hosts to obtain IPv6 addresses and routing information from an ISATAP router to support manage out for DirectAccess clients.

ISATAP

When DirectAccess is installed, the server is automatically configured as an ISATAP router. Guidance for configuring ISATAP clients can be found here. Using ISATAP can be an effective approach to enabling DirectAccess manage out for SCCM when native IPv6 is not available, but it is not without its drawbacks.

• Using the DirectAccess server for ISATAP is only supported with single server DirectAccess deployments.
• Using the DirectAccess server for ISATAP does work when using Network Load Balancing (NLB) with some additional configuration, but it is not supported.
• Using the DirectAccess server for ISATAP does not work when an external load balancer is used, or if multisite is enabled.

ISATAP with Load Balancing and Multisite

It is technically possible to enable DirectAccess manage out for SCCM using ISATAP in load-balanced and multisite DirectAccess deployments, however. It involves deploying a separate ISATAP router and some custom configuration, but once in place it works perfectly. I offer this service to my customers as part of a consulting engagement. If you’re interested in restoring DirectAccess manage out functionality to support SCCM remote control, RDC, or VNC in load-balanced or multisite DirectAccess deployments, fill out the form below and I’ll provide you with more information.

Additional Resources

ISATAP Recommendations for DirectAccess Deployments
DirectAccess Manage Out with ISATAP Fails on Windows 10 and Windows Server 2016
DirectAccess Client Firewall Rule Configuration for ISATAP Manage Out
Video: Windows 10 DirectAccess in action (includes manage out demonstration)