When you take a look at Windows Server 2008, you’ll discover big changes — including some legitimate improvements.  Justin James outlines a few of the unexpected aspects of the new OS, both good and bad.

Windows Server 2003 felt like a refresh of Windows Server 2000. There were few radical changes, and most of the improvements were fairly under the surface. Windows Server 2008, on the other hand, is a full-size helping of “new and improved.” While the overall package is quite good, there are a few surprises, “gotchas,” and hidden delights you will want to know about before deciding if you will be moving to Windows Server 2008 any time soon.

Note: This information is also available as a PDF download.

#1: The 64-bit revolution is not complete

There have been 64-bit editions of Windows Server for years now, and Microsoft has made it quite clear that it wants all of its customers to move to 64-bit operating systems. That does not mean that you can throw away your 32-bit Windows Server 2008 CD, though! Over the last few months, I have been shocked on more than one occasion by the pieces of Microsoft software that not only do not have 64-bit versions, but will not run under a 64-bit OS at all. This list includes Team Foundation Server and ISA Server. If you are planning on moving to 64-bit Windows Server 2008, be prepared to have a 32-bit server or two around, whether it be on physical hardware or in a VM.

#2: Who moved my cheese?

While the UI changes in Windows Server 2008 are not nearly as sweeping as the Aero interface in Vista, it has undergone a dramatic rearrangement and renaming of the various applets around the system. In retrospect, the organization of these items is much more sensible, but that hardly matters when you have years of experience going to a particular area to find something, only to have it suddenly change. Expect to be a bit frustrated in the Control Panel until you get used to it.

#3: Windows Workstation 2008 might catch on

In an odd turn of events, Microsoft has provided the ability to bring the “Vista Desktop Experience” into Windows Server 2008. I doubt that many server administrators were asking for this, but the unusual result is that a number of people are modifying Windows Server 2008 to be as close to a desktop OS as possible. There have always been a few people who use the server edition of Windows as a desktop, but this makes it much easier and friendlier. These home-brewed efforts are generally called “Windows Workstation 2008,” in case you’re interested in trying it out on your own.

#4: Hyper-V is good, but…

Hyper-V was one of the most anticipated features of Windows Server 2008, and it’s surprisingly good, particularly for a version 1 release from Microsoft. It is stable, easy to install and configure, and does not seem to have any major problems. For those of us who have been beaten into the “wait until the third version” or “don’t install until SP1” mentality, this is a refreshing surprise.

#5: …Hyper-V is limited

Hyper-V, while of high quality, is sorely lacking features. Considering that it was billed as a real alternative to VMWare and other existing solutions, it is a disappointment (to say the least) that it does not seem to include any utilities for importing VMs from products other than Virtual PC and Virtual Server. Even those imports are not workaround-free. Another real surprise here is the lack of a physical-to-virtual conversion utility. Hyper-V may be a good system, but make sure that you fully try it out before you commit to using it.

#6: NT 4 domain migration — it’s not happening

If you have been putting off the painful migration from your NT 4 domain until Windows Server 2008 was released, don’t keep waiting. The older version (3.0) Active Directory Migration Tool (ADMT) supports migrations from NT 4, but not to Windows Server 2008. The latest version (3.1) support migrations to Windows Server 2008, but not from NT 4. Either migrate from NT 4 before changing your domain to be a Windows 2008 domain or get your NT 4 domain upgraded first.

#7: The ashtrays are now optional

In prior versions of Windows Server, a lot of applications came installed by default. No one ever uninstalled them because they did not cause any harm, even if you didn’t use them or installed an alternative. Now, even the “throwaway” applications, like Windows Backup, are not installed by default. After installation, you need to add “features” to get the full Windows Server suite of applications. This can be frustrating if you are in a hurry, but the reduced clutter and resource overhead are worth it.

#8: Licensing is bewildering

Continuing a hallowed Microsoft tradition, trying to understand the licensing terms of Windows Server 2008 feels like hammering nails with your forehead. So maybe this isn’t so much a surprise as a gotcha. The Standard Edition makes sense, but when you get into the issues around virtualization in Enterprise and Datacenter Editions, things can be a bit confusing. Depending upon your need for virtual machines and the number of physical CPUs (not CPU cores, thankfully) in your server, Enterprise Edition may be cheaper — or it may be more expensive than Datacenter Edition. One thing to keep in mind is that once you start using virtual machines, you start to like them a lot more that you thought you would. It’s easy to find yourself using a lot more of them than originally expected.

#9: There’s no bloat

Maybe it’s because Vista set expectations of pain, or because hardware has gotten so much cheaper, but Windows Server 2008 does not feel bloated or slow at all. Microsoft has done a pretty good job at minimizing the installed feature set to the bare minimum, and Server Core can take that even further. Depending upon your needs, it can be quite possible to upgrade even older equipment to Windows Server 2008 without needing to beef up the hardware.

#10: Quality beats expectations

Microsoft customers have developed low expectations of quality over the years, unfortunately, with good reason. While its track record for initial releases, in terms of security holes and bug counts, seems to be improving customers are still howling about Vista. As a result, it has come as a real surprise that the overall reaction to Windows Server 2008 has been muted, to say the least. The horror stories just are not flying around like they were with Vista. Maybe it’s the extra year they spent working on it, or different expectations of the people who work with servers, but Windows Server 2008 has had a pretty warm reception so far. And that speaks a lot to its quality. There is nothing particularly flashy or standout about it. But at the same time, it is a solid, high quality product. And that is exactly what system administrators need.