Despite years of delays, the reputation of Microsoft's Windows Server 2008 product has never really been sullied like that of Windows Vista. There are valid reasons for this: Windows 2008, as a server product, can afford the slow burn because its biggest customers will upgrade on their own slow schedules anyway. It's interesting to me, though, that the Windows Server guys have largely escaped the criticisms that dogged, and continue to dog, the Windows client side. And now, with Windows 2008 set to ship a whopping five years after the previous major server release, the company has announced a bewildering and complex amount of information about the pricing, packaging, and licensing for the product. And suddenly, everything is a mess.

First, the good news: The various Windows 2008 product editions will cost approximately the same as their Windows Server 2003 predecessors. (Microsoft says the average price increase is 1 percent.) So there's no massive price hike here despite the myriad of new features and functionality. Also, Microsoft promises no more delays. Windows 2008, I was told, will ship in time for the February launch event.

Well, sort of. As it turns out, key versions of Windows 2008 won't actually ship anywhere near February, though to be fair, this was previously known. More problematic, in my mind, is that Microsoft is bifurcating its Windows Server product line in a way that resembles what the company did with Windows Vista and Office 2007. It's also charging customers for key management technologies that, frankly, should be included in the base product for free. Good luck keeping this all straight.

First, mainstream editions of Windows 2008 will be sold in versions that do and do not include Microsoft's virtualization technology, which has been renamed yet again to Hyper-V. (Previous monikers included Viridian and Windows Server Virtualization.) So the Windows 2008 product line breaks down as follows:

Windows Web Server 2008: $469
Windows 2008 Standard: $999 with five Client Access Licenses (CALs)
Windows 2008 Standard without Hyper-V: $971 with five CALs
Windows 2008 Enterprise: $3,999 with 25 CALs
Windows 2008 Enterprise without Hyper-V: $3,971 with 25 CALs
Windows 2008 Datacenter: $2,999 per processor
Windows 2008 Datacenter without Hyper-V: $2,971 per processor
Windows 2008 for Itanium-based Systems: $2,999 per processor
Hyper-V Server: $28, no parent OS included

Looks straightforward, right? Not exactly. First, notice that the versions without Hyper-V are only nominally less expensive than those that ship with the technology. It's unclear why they're shipping versions of Windows 2008 Standard, Enterprise, and Datacenter that don't include Hyper-V, as it's an optional install anyway. But now I'm going to blow your mind: The product line is actually even more complex than what's listed here. That's because Microsoft is actually selling different 32-bit and x64/64-bit versions of most of these products, except for Windows 2008 for Itanium-based Systems, which will ship only on the 64-bit Itanium platform. (That's right, you can now get Web Edition in 64-bit form for the first time.) And Hyper-V is available only on x64 versions of the system. Unless of course you get a "without Hyper-V" version for some reason.

Yikes.

If I'm counting right, there are actually 15 or 16 different versions of Windows 2008 you could install, depending on whether you include the standalone version of Hyper-V Server as a version of Windows 2008 which, arguably, it is not.

Because the Hyper-V technologies won't ship until 180 days after the Windows 2008 release to manufacturing (RTM), Microsoft won't be selling many of these products until mid- to late-2008. According to the company, the "without Hyper-V" versions of Windows 2008, and Hyper-V Server, won't ship until this time. (It's unclear why they can't ship "without Hyper-V" versions immediately.) Here's the final gotcha. Although Windows 2008 will ship with single server Hyper-V management tools when those technologies become available sometime in 2008, Microsoft is selling a separate tool called Virtual Machine Manager (VMM) that will help manage multiple installations of the server from a single console. Today, VMM works only with Virtual Server 2005 R2, but it will be updated in 2008 to support Hyper-V. You might be shocked to discover that customers who purchase non-Software Assurance (SA) versions of this software will actually be charged again next year for the Hyper-V upgrade to VMM. That's ridiculous.

In short, this is a mess, a big, unhappy mess. I'm excited about Windows 2008 and the functionality it brings to the party, but I'm a bit freaked by this sudden and confusing explosion of information. I can only imagine how confusing this is to Microsoft's customers, and I have to say, I don't feel like I'm doing much to add clarity to this picture at all.