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.

14 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………..

  12. ArkiTek Says:

    I too, had this problem and was able to get WinServ 2008 up after having the same problem.

  13. james miksi Says:

    in my situation i had the vm booting/installing from an iso of 2008 x64. after choosing “Install Now” the first thing i was being asked for was the product key- which entailed the aforementioned error and inability to install. was attempting to use a MKS volume key.

    i re-copied my iso and was then able to proceed. most notably was that instead of first getting asked for a product key i was instead given a list of 2008 versions to install (std/ent, core, etc), then i was asked where to install (vhd) and then install began… no prompting for product key.

    in my case it appeared my iso was in fact bad.

  14. Francois Says:

    in my situation i had the VM booting/installing from an iso of 2008 x86. after choosing “Install Now” and it’s stop there with the following error message after I entered my volume license product key:
    Windows installation has encountered an error and needs to be restarted
    Of course, I thought it was my media but I copied the iso with Veam fast FCP from my laptop to the datastore vmimages folder on my vsphere 4 server and from there I deployed the VM windows 2008.
    Now it works well


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