Windows Server 2008 Installation Error: Windows installation has encountered an error and needs to be restarted

I was installing Windows Server 2008 Enterprise x64 on Monday, and the installation kept bombing out with the following error message after I entered my volume license product key:

Windows installation has encountered an error and needs to be restarted

I tried re-burning the .iso image, thinking I had a bad burn or defective media, but the install kept failing. I even went back and re-downloaded the same .iso image, but the results were the same.

I was finally able to get the install to succeed by choosing not to enter a Windows product key. Windows balks at not providing the key, but will allow you to continue the install.

After doing some research I found this post that mentions this installation problem is related to using a Technet/volume license key with a trial version of the OS.

11 Responses to “Windows Server 2008 Installation Error: Windows installation has encountered an error and needs to be restarted”

  1. Maurice Says:

    Hmmm… sounds exactly like my problem. I’m not sure which version of Win2K8Web server I got, I think the trial version. Got the key from eOpen.Microsoft.com.

    The problem is, does leaving off entering the key until after the install mean you just postpone the problem?

    I’m re-downloading the ISO from eOpen. Since it’s the palce that gives me the key, it should be the correct version of the software?

  2. Julie Says:

    After the install was complete we were able to activate Windows over the telephone, so you should be okay. Internet activation never did work.

    -Julie

  3. Vageesh Says:

    Julie,
    We are trying to download Win Server 2008 (64-bit) from last 10 days from Microsoft website but the site is giving some error. please let me know from where u downloaded?

  4. Mike Says:

    I had a similar problem and I found out the 5 gig of memory was too much for the installation. When I installed it on Vmware I allocated 1 gig and it loaded fine.

  5. west99 Says:

    thanks a lot, it helped me.

  6. Mark Says:

    Same issue with my key, did exactly the same as you, regarding re-writing and downloading, how annoying

    thanks!

  7. Devin Says:

    Whew! I thought I was going mad. Thanks OP for posting this information – I was having the exact same issue.

    -DC

  8. saar Says:

    Super post julie.

    Thanks.

  9. Brady Says:

    Very nice.

    A quick Google search led me here and confirmed that I was not alone.

    Thanks!

  10. JAB_au Says:

    You would think Microsoft would get something like there product keys right wouldn’t you.

  11. Chris Says:

    And another one with this issue………….

    I guess telephone activation is the way forward………..

    Ditto on the MS Key comment! Who would have thought that MS could not get thier own installations to work seemlessly. Hey ho………..


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