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unops
Contributor
Contributor

Upgrading Virtual Windows server 2003 to 2008

We currently run VI 2.5 with 3.5 U2 servers in a cluster. I was trying to upgrade (in place) a Windows server 2003 st. to Windows Server 2008. However when doing this the guest becomes unresponsive at (completely black screen in the console windows) and the setup reboot the guests and I boots back into 2003 (stating that the setup/upgrade failed). Is there a trick I need to be aware of?

18 Replies
Texiwill
Leadership
Leadership

Hello,

Moved to Virtual Machine and Guest OS forum.


Best regards,

Edward L. Haletky

VMware Communities User Moderator

====

Author of the book 'VMWare ESX Server in the Enterprise: Planning and Securing Virtualization Servers', Copyright 2008 Pearson Education.

CIO Virtualization Blog: http://www.cio.com/blog/index/topic/168354

As well as the Virtualization Wiki at http://www.astroarch.com/wiki/index.php/Virtualization

--
Edward L. Haletky
vExpert XIV: 2009-2023,
VMTN Community Moderator
vSphere Upgrade Saga: https://www.astroarch.com/blogs
GitHub Repo: https://github.com/Texiwill
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jfmartin
Contributor
Contributor

Hi,

Did you get any answer to your question? How did you solved your problem... because we have questions ourselfs that fall in the same kind of issues....

JF Martin

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doubleH
Expert
Expert

just thinking out loud....would you have to edit the vm settings to change it from windows 2003 to windows 2008 at some point during the upgrade?

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jfmartin
Contributor
Contributor

Hi,

Well, I would guess the answer is yes... we would need to set the OS type to match the actual OS running inside the VM. But, to do that, we need to stop the VM... so this pose a tricky action that needs to take place just before the VM reboot... we would need to power off the VM before the reboot completes... Again, I'm surprised that the Guest OS guide from VMware don't event talk about those issues... More and more people are going virtual and chances are that more and more people will need to do inplace upgrade for infrastructure servers since there is no obsoleteness in VMs...

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aswigon
Contributor
Contributor

Has anyone found a solution for this issue as I have the same problem? Does the change of guest type work?

Thanks.

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RParker
Immortal
Immortal

Has anyone found a solution for this issue as I have the same problem? Does the change of guest type work?

I'd say the problem was with the VM tools, during an upgrade. But the binaries for Windows 2003, 2008 are the same for installation, so it shouldn't matter if the VM was set for Windows 2008 or not, since that would only matter AFTER Windows 2008 was up and running. But turning off services, removing all programs BEFORE you start the install (like VM ware, and any programs you don't need) and since VM Ware uses drivers those drivers may not be compatible with Windows 2008 in fact I am sure they aren't. So that could be the problem.

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aswigon
Contributor
Contributor

After posting my initial reply I tested the upgrade after uninstalling VMware Tools. The upgrade proceeded flawlessly and it appears from the logs that the previous failures were due to the mouse driver. I hope this assists others.

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Hawksey
Contributor
Contributor

I'm having the same issue after Virtualization numerous 2003 Servers, we cannot upgrade them to 2008. This issue is only affecting Servers that have been P2V'ed. Tried removing VMware tools and all applications but still failing. Guessing it may be a hidden device/driver issue, but haven't been able to work it out yet.

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ChristopheC
Contributor
Contributor

Hi Hawksey,

We are experiencing the same problem. Did you find a solution to your problem ?

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gatornek
Contributor
Contributor

Someone being able to produce a 'fool-proof' method (ie "for me") on this would be great.  I'm trying to get about 30 machines done, and keep running into same problem where I get 80% of the way through the install, and then it decides to come back with an "unexpected error" in which it will proceed to rollback.  The only TIME I have been able to get to it successfully take the in place upgrade is when I completely uninstalled VMWare tools, disabled the "Base System Device" in Device Manager (aka VMWARE VMCI bus controller), and then change the Guest OS version type in the VM setting PRIOR to commencing the upgrade.  However, this same procedure which was a drop in the hat of over 50 attempts now...has not been proven fruitfull any other time.  It would be great if VMWare would chime in on this, but I'm sure they just want to take a 'blame windows and leave us alone' stance.

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Savienus
Contributor
Contributor

A big thanks to you my friend... I followed your steps and it actually works on my environment... currently I got 2-3 more Windows 2003 servers that needed to be upgraded to Windows 2008. However to save cost we are doing it ourselves... below is the steps I taken following your steps:

Do note that I did this in VSphere 4.0 Update 2 version. One more thing... Ensure you got at least 20GB HDD free space in boot drive before you do the steps below else it will be like me the first time doing it...

1. Windows 2003 VM - Remove/Uninstall the VMware Tools from the Control Panel.

2. Shut down the Windows 2003 VM. You do not need to restart because you need to change the Guest VM OS from Windows 2003 to Windows 2008 R2. Once the Guest OS is changed, start the Windows 2003 VM.

3. Suffer a bit on the screen resolution but you can tweak it back to 1024 x 768 using the default VGA drivers. Recommend to do this so that it would be easier to work with a bigger desktop.

4. Go to the Device Manager Tab to disable the "Base System Device". This took me a while to confirm the location because of the bad mouse (It will happen after VMware Tools is removed).

5. Proceed to do the Windows 2008 upgrade.

Hope this steps will help others...

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colyebm
Contributor
Contributor

I am also in the middle of the 2003 remediation... and had this issue.

I followed all of Savienus's instructions and it still failed, so i did some more searching around and realized as a big company trying to get all of our IT sites integrated with each other, we have migrated from domain to domain and again to another domain over the years and have had multiple SIDs for the same one user account... i found this post useful: Installation errors XP S2 to Vista home premium.

Down on Note 5:
"Vista Upgrade fails at "Gathering Files" when two users share the same user profile (ProfileImagePath). The fix is to go into HKLM\Software\Microsoft\Windows NT\CurrentVersion\ProfileList and find the SID of the extra/unnecessary user of the profile, and change their ProfileImagePath to something different. Doesn't matter if that path doesn't exist yet, a clean profile will be created upon logon."

So after taking some snapshots (just in case), and using Savienus's steps, i went in and deleted all of the SID Keys from this location and tried the install again. I got past the error and my Server rebooted and continued the upgrade process. couple hours later... I was able to sign into my updated 2008 server.

I also hope this will help someone else...

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geogherkins
Enthusiast
Enthusiast

Using tips in this thread as well as other research here are all of the steps I used to successfully upgrade Win2003 (32bit) VM to Win2008 (R1 32bit) VM.  This was used on vSphere 5.5.

In-Place Upgrade Windows 2003 (32bit) to 2008 R1 (32bit) Notes

1. VMware: Clone Windows 2003 candidate server to a new VM
2. VMware: Disconnect network adapter
3. VMware: Increase C: disk volume by at least 20GB (must have 20GB free space)
4. VMware: Power on cloned machine
5. Win2003: Logon local Administrator account (no network available)
6. Win2003: Uninstall all unnecessary applications before beginning
   a. Uninstall Backup Client Agent
   b. Uninstall AntiVirus Client
   c. Uninstall Management Agent
   d. Uninstall VNC
   e. etc.
7. Win2003: Restart
8. Win2003: C: Disk Properties > run Disk Cleanup
9. VMware: Optional snapshot server for baseline safety copy to resume here.
10. Win2003: Extend C: (Parted Magic ISO, or whatever method you like) to include new 20GB free space
11. Win2003: Restart (CHKDSK may automatically run)
12. Win2003: Validate functional OS (look at event logs)
13. Win2003: Uninstall VMware Tools
   a. Uninstall VMware Tools
   b. Uncheck VMware: Edit Settings > Options > VMware Tools > Advanced > upgrade Tools during power cycling
   c. Restart
14. Win2003: Cancel PnP device manager driver Wizard
15. Win2003: Manage Computer > Device Manager > Base System Device > Uninstall
16. Rename PowerShell folder located at: %windir%\System32\WindowsPowerShell to 2003WindowsPowerShell
17. Win2003: Shutdown
18. VMware: Optional snapshot server for baseline safety copy to resume here.
19. VMware: Edit Settings > Options > Guest OS: change from Windows 2003 (32bit) to Windows 2008 (32bit)
20. VMware: Power on
21. Win2003: Cancel PnP device manager driver Wizard
22. VMware: Connect CD/DVD to Win2008 ISO 
   a. Note bug in vSphere client, you may have to close all vSphere client application sessions and/or restart your PC to connect to CD/DVD ISOs if you have had several connections during this session already
23. Win2003: Autorun.exe from Win2008 x86 ISO install DVD
24. Win2008 Setup: Select > Do not get the latest updates
25. Win2008 Setup: Standard x86 > Next
26. Win2008 Setup: Accept License Terms > Next
27. Win2008 Setup: Which type of installation do you want? > Upgrade
28. Win2008 Setup: Compatibility Report > Next
29. Win2008 Setup: Upgrading Windows … Gathering files …
   a. Elapsed time approximately 20 minutes
30. Win2008 Setup: Automatic restart
   a. Expanding files …
   b. Installing features and updates …
   c. Completing upgrade …
   d. Elapsed time approximately 10 minutes
31. Win2008: Automatic restart
   a. Boot Manager Menus
      i. Earlier Version of Windows
      ii. Microsoft Windows Recovery Console
      iii. Tools: Windows Memory Diagnostic
      iv. Windows Server 2008 (automatic selection 30 second timeout)
   b. Please wait while windows sets up your computer …
   c. Elapsed time approximately 5 minutes
32. Win2008 Setup: Automatic restart
   a. Completing upgrade …
   b. Elapsed time approximately 10 minutes
33. Win2008 Setup: Automatic restart
   a. Please wait while Windows continues setting up your computer …
   b. Elapsed time approximately 5 minutes
34. Win2008 Setup: Automatic restart
35. Win2008: Logon as Administrator
   a. PnP pop-up Found New Hardware > Ask me again later
   b. VMware: VM > Guest > Install/Upgrade VMware Tools
36. Put new system into production
   a. Choose this fork if the upgraded machine will simply replace the original
      i. Win2003: Shutdown original machine that you copied
      ii. VMware: Enable network adapter
      iii. Win2008: Confirm network properties (IP address, DNS, etc.)
   b. Choose this fork if the upgraded machine will be an entirely new machine on the network
      i. Win2008: Rename cloned computer (had you planned in advance, the VMware cloning Wizard will change the SID, name the machine to a new name, set network settings, etc. for you at the time you create the machine copy)
      ii. Win2008: Change SID using Sysprep (will restart x2)
      iii. Win2008: Rename computer
       iv. VMware: Enable network adapter
      v. Win2008: Set network properties (IP address, DNS, etc.)
      vi. Win2008: Add to domain
      vii. Win2008: Restart
37. Move computer to correct OU in AD, wait for AD replication
38. Win2008: CMD > GPUPDATE /FORCE
39. Win2008: Run Windows Updates (multiple restarts)
40. Win2008: Install required software
   a. AntiVirus Client
   b. Management Agent
   c.  Backup Agent
   d. etc.
41. Win2008: Thoroughly test all applications on upgraded server
42. VMware: Snapshot manager (delete optional safety snapshots you made earlier)

Thanks to these threads for additional information:

http://williamfaulkner.co.uk/2013/02/server-2003-to-server-2008-upgrade-powershell-compatibility-err...

http://social.technet.microsoft.com/Forums/en-US/winserverMigration/threads

https://technet.microsoft.com/en-us/library/cc755199(v=ws.10).aspx

Lessi001
Enthusiast
Enthusiast

Only for the sake of completeness:

Inplace upgrades of the guest OS is not supported by VMware - take a look at VMware KB: VMware support for guest operating system upgrade

There are 10 types of people in this world. Those who understand binary, and those who do not.
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rlascasas
Contributor
Contributor

for those of you still without the guts to upgrade your 2003 servers to 2012, and want to take the easy way out for sake of moving to 2008 and stave off the end of life for a few more years... I ran into the same issue on some neglected 2003 servers to be bumped up to 2008; i noticed that the server continued to ping during the expanding files step, which is odd... so i did a hard shut down of the vm, restarted, restarted in place upgrade... during the expansion of files step the server stopped pinging (good sign as it tells me it's ignoring the nic connection) after rebooting automatically, and continued to finish the upgrade splendidly... in place upgrades make me nervous as you really don't know how long to wait out potential issue, a lot of praying goes with it... this is my last of 2003 in my farm thank God, next time around will fight with robocopy on 2012 migrations, wish i could take retirement by then.

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Wavestone
Contributor
Contributor

geogherkinsHello geogherkins,



a question - regarding adding a CDRom, lets say i have  enough space on other partition on the VM, is it recommended\possible to upgrade the VM though copying the installation files locally ? lets say D drive ?



thanks

Gal Sela,

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GeorgePerkins
Contributor
Contributor

Gal Sela,

Yes I think you can just copy the install media locally to another partition. You won't have to boot from the CD. Just do the in-place upgrade from Win2008 Setup located on your other partition. But why not just attach an ISO of your Win2008 media to your VM's CDROM?

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rpas2915
Contributor
Contributor

Thanks a lot!

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