if NT4 Server ain't broke, don't Windows 2008 fix it?

Microsoft supported Windows NT4 Server from release to manufacturing in 1996 to the last fixes in 2004. Astonishing numbers of servers reportedly still run NT4 Server, including two that I manage: one is a file/print/directory server and the other is a hot spare for the first one. Both are behind a firewall, and neither is used for email or browsing or other applications likely to be vulnerable to Internet compromise. They’re mostly trouble free. So if it ain’t broke, why fix??

That was the question in early 2004, before the end-of-life of NT4, when Windows Server 2000 was being supplanted, at least in Microsoft’s plans, by Windows Server 2003. At that time, my experience with Active Directory supporting old NT domains had been frustrating. In principle, Active Directory in Server 2000 supported NT domains, but in practice, Server 2000 didn’t seem ready to do that. In 2004, trying Server 2003 made sense, thinking that A.D. should work better than in Server 2000, but it wasn’t clear that Server 2003 would be robust enough until after the first service pack (which was not released until March 2005). Attempts to test a gratis copy of Small Business Server raised even more directory concerns.

Fast forward to today. Windows Server 2008 is available, based on much code shared with Windows Vista. Vista Service Pack 1 is available. Our production NT4 Server is supporting some Vista clients, mostly without difficulties. However, less expensive versions of Vista don’t support Group Policy Editor. Vista won’t use NT4 printer drivers without changing settings with Group Policy Editor. So the nice big printer associated with the NT4 server isn’t available to typical Vista clients unless/until NT4 is displaced or a printer workaround is found.

I downloaded an evaluation copy of Windows Server 2008. For whatever reason, the first several downloads resulted in corrupt DVD images. When a download was a third the nominal size, it was obvious that something had gone wrong. But two seemingly complete downloads didn’t reveal corruption until install options failed due to missing files. Why doesn’t Microsoft provide check sums?? The most recent download seems OK, but it would be nice to have some confirmation.

The hot spare NT4 server is actually running as a virtual machine on VMware Server 1.0.2. My initial plan was to clone the NT4 server and upgrade it with the Server 2008 disc. However, the Server 2008 disc file system is ISO-13346 “UDF” format, which is not readable by either NT4 or VMware Server 1.0.2. Upgrading to VMware Server 1.0.5 allowed fresh install of Server 2008. However, the initial install of Server 2008 would not join the existing NT4 domain. I need to do some more tests to understand that.

Another obstacle to upgrading a clone of the NT4 server is that machine’s primary partition is only 2GB. Server 2008 (and Server 2003) recommend larger partitions and probably won’t reasonably upgrade in that partition.

So I’ve also downloaded a Server 2003 evaluation copy. That installed OK on VMware Server 1.0.5 and joined the existing domain without difficulty. I cloned that Server 2003 machine and upgraded the clone to Server 2008. Both the Server 2003 and Server 2008 seem to be proper domain members.

So now the priority is to enable Active Directory in the Server 2003 & Server 2008 machines and see how that works. Also, I need to try another non-upgrade install of Server 2008 and see if that will join the domain, etc.

I expect that fiddling with all of this will take weeks, if not months. In the mean time, NT4 will likely serve just fine…

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