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In place upgrade windows server 2003 standard to 2008 standard

Hi experts,
I am trying to perform in place upgrade from windows server 2003 standard to windows server 2008 standard,  during the upgrade completion I received the following error:

"Windows installation encountered an error and can not continue. Your computer will now restart, and your previous version of windows will be restored".
While I click Ok the installation procedure did not move forward rather it restore existing OS windows server 2003. I am trying it third time but still no luck. I have uninstalled antivirus from the server 2003 but still receiving the above error.  I am trying to perform the upgrade in VM environment.

 Can you please advise, what steps I am missing or what needs to be done to complete the upgrade successful.
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ipsec600
Asked:
ipsec600
2 Solutions
 
Matthew BorrussoCommented:
You have a couple of things to check.

1. ensure you hypervisor version supports the new operating system. for example VMware vsphere 4 does not support 2012 server. make sure your version is supported.
2. You may need to upgrade 2003 x32 bit to 2008 32 bit. make sure you have the right version.
3. Make sure your vm meets at least the minimum requirements for the system.

If my memory serves me correct, you cannot go to 64bit from a 32bit os, I could be wrong, but google can confirm that for you.

Since its virtual, it may be easier to spin up a new guest and install 2008 clean. then DCpromo and move the 5 roles over to the new server. You can then three card monty the servers. to explain. Take 3 address for the 2 servers. lets say the 2003 server lives on .10. put the new server on .11. when everything is built and tested, move the 2003 server .12 (update your dns to ensure ddns records update) and reboot. when everything is stable, move the new 2008 server from ,11 to .10. update DNS and bounce it. once it comes back, verify everything is in order and synchronized. update the DNS info on the old server just in case and then you can power it down to put in a decommission hold for whatever time length you want to hold in case anything has a problem.

I would be very surprised if one of these solutions does not work out well for your needs.

Luck,
Matt

Also: Backup your AD!!!! I have had domain controllers not come back on me before, so better safe than sorry.
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ipsec600Author Commented:
Hi Matt, thanks for your quick reply and excellent clarification, I am trying to upgrade from Windows server 2003 32 bit standard edition to windows server 2008 32 bit standard edition. And I am not performing upgrade to domain controller rather its an application server which is member of a domain. During upgrade it checks minimum requirement and if that satisfies then upgrade proceed for next steps, and in my case minimum requirement meets.

Not sure what I am missing that is preventing to complete the ugprade, C: drive free space is 12GB, which should be fine, Can you please advise more. thanks
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
It's possible the upgrade is not compatible, I would check with Microsoft Support.
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rindiCommented:
Make sure you have run all windowsupdates on your old OS. Also run a chkdsk /f /r on your files-system before starting to fix any corruptions there may be on it. Stop any services, particularly if they are 3rd party. 12GB free space, in my point of view, is very low for an upgrade. Windows 2008 when installed may just about fit onto 12GB, but then there is no room for temporary files needed during the installation, and besides that, your old OS is kept when upgrading.
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Matthew BorrussoCommented:
Sorry, For some reason, I had the domain controller upgrade stuck in my head.

I agree with Rindi.

Usually, when the space is the problem the install should throw that flag, but I would confirm that to be safe.. Run through the basics, like the chkdsk and increase the space if you can. One last item to try, depending on the application thats running, kill all the services associated before you start the upgrade. Depending on your app, that could bite you.

It could also be a driver issue, if you do the windows updates (as per rindi) and also make sure your hyper-visor integration tools are up to date (IE vmtools, hyperv integration services, etc).
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hecgomrecCommented:
First of all I will never do an in-place upgrade on a VM or Metal Box.

If you want to avoid problems, it is always advisable to perform a clean install separate and migrate/move all services (roles) to the new server.

If you still want to go that path you have to make sure of the following: https://technet.microsoft.com/en-us/library/dd979563(v=WS.10).aspx

Also, please!!!! move to 64 bits software.... is good for you!!!
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Matthew BorrussoCommented:
I don't disagree with you on the in-place upgrade. There is all sorts of grief associated with this.

However, the user may not have a choice. I have to assume (i know what they say about assume), that a clean server and move the application was not an option or a reasonable option. I have upgraded many a windows server but my goal was to always decommission the upgraded server in lieu of a new clean install on a fresh box.

If he runs through the steps of updates, the space and disk check, a good reboot, and then kills the services and starts his process, by rights this should go through.

I would of course clone the box just to be safe before doing anything (i dont know if I would trust a snapshot in order to be able to revert quick here).
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ipsec600Author Commented:
Hello All, thanks for your reply and apology for replying late, I tried to upgrade two servers and it was successful for two servers and only issue I notice with the C: drive disk space, as soon as I increase space in the drive, the issue fix and upgrade was successful.

Now I am struggling for other servers with has not enough disk space in C: drive but C:\ drive is the dynamic disk. I am not sure how to increase dynamic disk, do you guys have any idea? Can I use any third party software though I found the one in the URL
http://www.partition-tool.com/resource/extend-windows-server-dynamic-disk.htm

Thanks,
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ipsec600Author Commented:
Hi Guys, I will open separate thread for this remaining issue, but the actual reason I have opened this questions is resolved. Thank you all for your help.
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