I found similar questions but in reality I have to justify why I really need 2008. I have 2003 and other than it's nine-years-old, I found it wouldn't do ASP.MVC and I am sure many other things. I'm sure I'm not specific enough. I was hoping for something...

  • things I can come up with AD is better, but I don't know why.
  • Security better, but I don't know why
  • faster? I have no idea.
  • better IIS. Is this really true?

Not sure really why one is better than the other.


  • Aside: Server 2003 will do ASP.NET MVC, you just need to install it. I had Server 2003 with ASP.NET MVC 3 in a VM only last week. I did have to install .NET 4 and the MVC files, but that was about it. – Ben Pilbrow Jul 18 '11 at 22:06
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    Why the down vote with no comment? bad form. – johnny Jul 18 '11 at 22:25
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    Sounds like you need to do some research on your own and come back when you have a real question. – MDMarra Jul 18 '11 at 22:26
  • Johnny, there's not really much of a question here, and there's sort of 5 half-questions. If you have a very specific question that can actually have a objective answer, please update your question, otherwise I don't think you'll find what you're looking for. – Mark Henderson Jul 18 '11 at 22:53
  • @mark I disagree but okay. – johnny Jul 19 '11 at 18:04

I'd say age is the biggest factor here. The fact you're even thinking about not buying the current version of the operating system (seemingly without good reason) is crazy to me, but that's my opinion I guess. Also, when you say Windows Server 2008, I hope you actually mean Windows Server 2008 R2.

More importantly however, the final set of security updates for Windows Server 2003 will be released on July 14th 2015. That's only 4 years away and will come round so much quicker than you think. Unless you can be absolutely certain the server will be replaced before the operating system reaches end of life, you'll be running production (and I'm guessing business critical) applications on an unsupported and vulnerable operating system before you know it.

Not only is Microsoft going to shun you when something breaks, so will your application vendors. If you have any kind of problem, you are pretty much up the proverbial creek without a paddle.

Then you've got your security problems. There WILL be vulnerabilities, and Microsoft WILL NOT patch them. Try explaining to your boss that your server is down because it's been hacked. Then try to explain that when you re-install Windows, the attackers can do it all over again because there is not and will never be a patch to fix the underlying security problem.

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    Not to mention that the cost of bringing an out-of-date system up to current becomes increasingly expensive over time. Consider the cost of upgrading from Exchange 2007 to Exchange 2010 versus upgrading from Exchange 2000 to Exchange 2010. Supported upgrade paths also become fewer as time drags on. – Chris Thorpe Jul 18 '11 at 22:46
  • Good stuff, I agree with it personally 100%. I wish I saw more vendors agreeing with the Vendors shunning the OS. I know some that aren't even close to supporting 2008 yet, and at least 1 that still uses 2000. I wish they would die. – Nixphoe Jul 19 '11 at 1:34

With Windows 2008 Enterprise (and enough RAM), you could run up to 4 Enterprise Windows VMs with Hyper-V. You could also Physical-to-Virtual (P2V) your existing Windows 2003 server for running any applications that won't run on Windows 2008.

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  • But why would I want to run 4 enterpise windows server iterations like that? – johnny Jul 18 '11 at 22:19
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    Why not? Beats buying 4 physical servers. – gravyface Jul 18 '11 at 23:23
  • because then my single point of failure is the same machine. If that goes down I lose everything. – johnny Jul 19 '11 at 13:51

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