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I just bought a fresh retail copy of Windows Web Server 2008 from newegg the other day for a small web server I'm setting up at home. Went to install it, and it told me the license key was invalid.

Of course I thought I must have just mistyped it, but after checking and re-checking 5 or 6 times, no dice. I called Microsoft support, read them the key, and they said it was valid and further "support" on this issue would cost me $259. Called Newegg as well, and of course they said to call Microsoft.

Has anyone else had issues with Windows Web Server 2008 rejecting valid license keys? Is there anything I can do about this other than return it and hope the next copy I get works?

If it matters, I'm installing the 64 bit version. The retail copy comes with 32 and 64 bit versions, but my understanding is that the key should work for both. Also, I did enter the "phys" key, not the virtual key.

ETA:

Apparently others are having this issue as well.

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Have you rung them and confirmed that the key is valid for Windows Web Server 2008 and not just a valid key? –  Wayne Aug 6 '09 at 5:18
    
@Wayne - Yes, I believe Microsoft support did say it was a valid Windows Web Server 2008 key. I don't recall asking them that specifically, but during the call I verified with him a couple of times that it was Windows Web Server 2008 that I was installing. I think if the key was for another version he would have mentioned that at that point. –  Eric Petroelje Aug 6 '09 at 12:04
    
Is the same key valid for both 32 & 64? You said you think it is but are you 100% sure? –  SpaceManSpiff Aug 6 '09 at 12:20
    
@SpaceManSpiff - It should be the same key, although I can't seem to find anything that would verify that beyond any doubt. The retail box came with two dvds - a 32bit and a 64bit but only one license key. Nothing on the key label specified whether it was for the 32 or 64 bit edition. –  Eric Petroelje Aug 6 '09 at 12:47
    
If it's reassuring at all, when I pull up my MSDN subscription, the keys for 2008 Web are identical for x86 and x64 - so it seems that you're right on that count. –  Kara Marfia Aug 6 '09 at 13:01
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4 Answers

I know this is left field but do a memory check on the machine. I've had issues like this because the ram was buggered and it was causing the computation to fail.

Also the keys can be very fiddly when it comes to the edition they're for. If the key is for a specific windows SKU it wont install if you use the wrong disc or the wrong edition of the disc (eg using a windows XP key with an XP SP2 disk will not work).

Also with microsoft support, if you prove they screwed up, they waive the fee. If you have a disc from microsoft saying web server 2008, a key which they themselves say is legit AND you can get them to the installer where it declines it they will waive the fee and provide a new key for you.

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Doesn't seem to be a memory issue - I just tried removing all but one stick of memory, enter the key again, no go. Tried swapping that stick with another, also no-go. So unless both sticks are bad, it wouldn't be that. As for trying Microsoft support - not sure I want to bet $250 on them admitting they were wrong :) –  Eric Petroelje Aug 5 '09 at 23:59
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Make sure the date on your computer isn't way off. I've had trouble with either the key or activation (can't remember which one) and had to adjust mine.

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Good idea, but the date is correct. –  Eric Petroelje Aug 5 '09 at 23:44
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(idiot answer) I would try again, especially check for B and 8 as I am always having problems with them.

(smart answer) If you are 100% sure and it is a error, take it back to newegg as a faulty good and tell them to test it, then purchase another for yourself.

Maybe just to rule out anything on your machine, test it in a VM first.

I have installed Windows web server a few times, but I copied and pasted my serial key from technet and have not had these problems you speak of, but I have them all the time when installing office when I am at a client.

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@Wil - Yeah, thought about the B vs. 8 thing, and checked that as well. I'm in the process of RMA'ing it now, but my biggest concern of course is that when I finally get a new copy, that the new one won't work either... –  Eric Petroelje Aug 6 '09 at 12:06
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You should be able to install Windows 2008 completely bypassing the license key (just click next) to get you going. Once you have Windows up and running, try entering the key by right clicking My Computer/Properties. If you still have no joy, I would call the Microsoft licensing activation number rather than the general product support number. The relevant phone numbers are here:

http://www.microsoft.com/licensing/existing-customers/activation-centers.aspx

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Thanks Alex - I did skip the license key and got it installed. I tried putting in the key again once the install was complete (and after running windows update), but no joy. I've RMA'd the software to newegg and if it still doesn't work when I finally get a new copy, I'll try calling the activation number once to see if they can help. –  Eric Petroelje Aug 28 '09 at 11:56
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