SharePoint Notes

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Upgrading a MOSS Farm from Windows Server 2003 to Windows Server 2008

Posted by Christian Dam on February 9, 2008


Despite Microsoft’s recommendations to to a complete re-install when upgrading Windows Server 2003 servers if they contain software not included in original installation media or in a following service pack, I decided to give it a go anyway.

As you may know, my farm is hosted on a physical server running Windows Server 2008 Enterprise (Full) and Hyper-V. The farm components are:

  • One Active Directory server
  • One Web Front-end
  • One Application/Index server hosting the central Administration
  • One SQL Server back-end

All farm servers are running Windows Server 2003 Enterprise x86 editions and no additional software other than MOSS, SQL Server 2005 and a MOM 2007 agent. MOSS is running SP1.

The upgrade was performed in the following order

  1. Active Directory
  2. SQL Server back-end
  3. Application server
  4. Web Front-end 

Before I began, I made sure I had a fresh snapshot of every server in case something goes wrong … as I expected it would …

Active Directory:

  1. Start up the server
  2. Check the levels of warnings and potential errors in the event log
  3. Insert the DVD 
    • To perform this procedure, you must use an account that has membership in all of the following groups:
      • Enterprise Admins
      • Schema Admins
      • Domain Admins for the domain that contains the schema master 
    • To prepare the forest schema for Windows Server 2008
      • Log on to the schema master as a member of the Enterprise Admins, Schema Admins, and Domain Admins groups
      • Copy the contents of the <DVD ROOT>\sources\adprep folder to an Adprep folder on the schema master
      • Open a command prompt, and then change directories to the Adprep folder
      • At the command prompt, type the following, and then press ENTER:
        adprep /forestprep
      • If you plan to install an RODC in any domain in the forest, type the following, and then press ENTER:
        adprep /rodcprep
      • Allow the operation to complete, and then allow the changes to replicate throughout the forest before you prepare any domains for a domain controller that runs Windows Server 2008
  4. Run setup.exe from the DVD root if auto-play is not enabled
  5. Hit Install Now
  6. On the Get important updates for installation-window, make your choice. Being a happy little camper, I choose to help Microsoft to make the Windows installation better and to Go online and get the latest updates for installation.
  7. Select the operating system you want to install. Choose the same version as already installed on your server. I choose Windows Server 2008 Enterprise (Full Installation).
  8. Accept the license terms
  9. If all prerequisites are met (like having prep’ed AD correctly), the upgrade option is available. Hit Upgrade
  10. An upgrade warning is displayed. Ignore and click Next if you are brave like me 😉
  11. The automatic upgrade process begins. It took my Domain Controller about 70 minutes and 4 reboots to be upgraded.
  12. Check Server Managerfor errors and warnings. I noticed that a lot of errors and warnings were logging during the upgrade process, so I took a quick and dirty approach to check if the AD was working OK: I simply cleared the log, rebooted the server and waited a while before I re-checked the event logs
  13. I did not receive any new errors or warnings that I could not explain, so I concluded the upgrade went OK
  14. Additional check can be to verify that all users and computers are still in the Domain and that users can still login to the domain from a member server or computer.

Next in line is the …

SQL Server back-end:

  1. Start up the server
  2. Check the levels of warnings and potential errors in the event log
  3. Insert the DVD 
  4. Perform steps 5 through 14 as described for the Active Directory Upgrade above – except the ADprep-stuff, obviously
  5. After the completed installation, I got a lot of “.NET Runtime Optimization Service (clr_optimization_v2.0.50727_32) – Failed
    to compile”-errors in the application event log. Different sources (like this) suggested various things to try:

    • do a complete reinstall of SQL Server 2005
    • repairing ASP.Net 2.0
    • setting the Microsoft .Net Framework NGEN v2.0.20727_x86 service to automatic
  6. I changed the service state to automatic and rebooted the server and the error disappeared. Set service switched it self back to manual, but I haven’t seen the error again.

So far so good! Let’s proceed with the …

Application Server

  1. Start up the application server
  2. Start Central Admin to verify there is connection the SQL Server back end (just to sanity check the previous upgrade)
  3. Check the levels of warnings and potential errors in the event log
  4. Insert the DVD 
  5. Perform steps 5 through 14 as described for the Active Directory Upgrade above – except the ADprep-stuff, obviously
  6. Once the upgrade completes, check the event logs and try to access Central Administration and one of the portal sites.

Everything looks great! Feeling optimistic, let’s complete the upgrade with the final server, the …

Web Front-end!

  1. Start up the Web Front-end server
  2. Check the levels of warnings and potential errors in the event log
  3. Insert the DVD 
  4. Perform steps 5 through 14 as described for the Active Directory Upgrade above – except the ADprep-stuff, obviously
  5. Once the upgrade completes, check the event logs and try to access Central Administration and one of the portal sites.

That’s it! Everything is looking fine. MOSS is accessible locally and across the network. I do not say that this approach is recommended or in any way best practices, but I have shown that an upgrade may be a valid option. It should even be possible to upgrade a MOSS farm one server at a time while users is accessing the sites and thus limit the down time to the time where the SQL Server back-end is upgraded. In a production environment I would still prefer to do a clean reinstall if time and cost permits.

Happy upgrading 🙂

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