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Windows Server 2008 R2: Not your father's R2 upgrade

While Windows Server 2003 R2 failed to live up to its own hype, Microsoft's next R2 release is in many ways a completely different OS. Find out what's new in Windows 2008 R2, and why some of the new features and improvements could be well worth the upgrade.

If you've been around the IT block for more than a few years, then you probably remember Microsoft's last R2 upgrade. Windows Server 2003 R2 started out with a lot of promise but ended up adding relatively little in the way of compelling new features to the standard Windows Server 2003 platform. Long-desired updates, like Project Bear Paw for Terminal Services, didn't make the final cut into Windows Server 2003 R2, and a lot of the "new features" were of little interest to most IT shops. As a result, many organizations ultimately passed on the last R2 upgrade, choosing to wait for Microsoft's next whole-number release.

Yet like the venerable Oldsmobile, this time Microsoft has truly nailed the feature set with its next to-be-released R2 upgrade. Unlike 2003's R2, Windows Server 2008 R2 is something you'll be seriously considering for your environment.

Why? Remember back to the end of 2005 when that first R2 arrived. Rather than being a truly new operating system, R2 arrived as a de facto "disk two" of the Windows Server 2003 media. This less-than-titillating disk two installed a set of features to a Windows Server 2003 instance that was mostly useless to a lot of IT environments. Operating as a feature pack as much as an OS upgrade, if you didn't specifically need its new features, your installs rarely got past disk one.

Windows Server 2008 R2, however, arrives as a functionally different operating system. The new OS brings core kernel changes, such as the ability to address more processors and improvements to common management tools, like Server Manager. Server Manager can now remotely access other servers and is alone a compelling upgrade. A dramatically more useful Windows PowerShell experience nicely rounds out R2's abilities. Unlike the limited-use new features seen in the previous R2, these are cool and useful add-ons that are sure to accelerate your desire for an upgrade.

x64 stands alone

It's important to note that Windows Server 2008 R2 marks the end of Microsoft's support of 32-bit operating systems inside your data centers. Notwithstanding the fact that Windows 7 and Windows Server 2008 R2 share the same codebase, Microsoft has drawn a line in the sand with this release. This R2, and every future Microsoft server OS, will only be available as a 64-bit installation.

For most IT professionals – especially those in smaller, less-complex environments who enjoy newer hardware – this decision isn't likely to make waves in your infrastructure. Every new server-class machine available for purchase today is already at x64, at least those you would want in your data center, that is. So, if you're buying new server hardware, you're virtually assured to be able to support Microsoft's exclusivity.

It might, however, pose a barrier to those who still maintain older hardware or whose enterprise environments have more complex needs, and nowhere is this more prevalent than in the financial and healthcare industries. These industries have longstanding histories of rarely upgraded applications, homegrown apps, old drivers and application vendors that won't play the modern-day technology ballgame.

Because of the compatibility subsystems that are required to run older software architectures, Microsoft's move to x64 only will cause some pain for those organizations. Whereas the x86 version of Windows Server has always supported 16-bit applications through its Windows-on-Windows (WOW) subsystem, 16-bit support is simply not available in x64. This version does, however, include the WOW32 subsystem, which supports today's 32-bit applications running on 64-bit servers.

If your applications and drivers are all running 32-bit, do not fear. You'll have full support. However, if you're running those painfully old and out-of-support applications and drivers that are still stuck in 16-bit, the upgrade to Windows Server 2008 R2 will be a more painful experience.

Kick the tires

Microsoft hasn't completely left you out in the cold even if you are still running 16-bit apps and drivers. With Windows 2008 R2, the company has augmented the venerable Terminal Services with support for virtual desktop infrastructure (VDI) environments. In some circles, VDI has a bad name for enticing people down technology paths that cost more and support fewer users, but it is the perfect solution for retaining support for your ancient applications.

In R2, Terminal Services has been renamed Remote Desktop Services (RDS) in an effort to recognize its dual role in supporting your applications both old and new. This happens through RDS's simultaneous support of traditional Terminal Services applications as well as its new capabilities for brokering VDI sessions to users.

Microsoft's VDI – and one can argue VDI in general – is specifically designed to provide a platform for supporting problematic applications on older operating systems. RDS's VDI components do a fairly good job of providing an inexpensive platform for hosting just those applications. In an upcoming article, I'll talk in more detail about RDS and some of its new "wow" that IT pros are sure to appreciate.

Windows Server 2008 R2 enables some entirely new features out of the box. They are:

  • DirectAccess -- Amounts to a clientless and always-on VPN between your laptops on the Internet and your internal network.
  • BranchCache -- Augments file services with over-the-wire caching of files, which speeds up the effective connection between branch and main office by reducing the amount of data that is passed over your WAN wires.
  • AgileVPN -- Brings a higher level of availability to your VPN connections by allowing problematic VPN connections to re-route without loss of connectivity.

Those three new technologies are only the beginning, as enhancements have also been made to technologies like Windows Clustering, BitLocker, Network Access Protection, Offline Files, iSCSI Initiator, Hyper-V, Network Load Balancing and others.

In upcoming articles, I will explain these new and enhanced features in plain English and with an eye toward the ones you'll be excited about. The series will update your knowledge about Remote Desktop Services and Microsoft's entry into the world of VDI, Hyper-V's new capabilities and exciting updates in PowerShell. I'll also discuss DirectAccess and BranchCache in much more detail and help you to understand the expanded business and technical value of technologies like BitLocker, IIS 7.5 and Windows Server 2008's new core parking capabilities.

Like the vehicles of yesteryear, this R2 release truly isn't your father's Oldsmobile. It's a brand new race car with all the bells and whistles that are far more likely to compel you to upgrade. Now your job is to get out, kick the tires a bit, and settle into its plush bucket seats. With Windows Server 2008 R2, you're sure to be in for a good ride.

Next: Terminal Services grows up with Windows 2008 R2

Greg Shields, Microsoft MVP, is a partner at Concentrated Technology. Get more of Greg's Jack-of-all-Trades tips and tricks at

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