Migrate Windows 2000 to Small Business Server 2008

Posted: February 18, 2010 in Migration Guides, Small Business Server 2008, Windows 2000
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If your simply here to find out if this is possible then take it from me the answer is most definitely NO! Well not if you want a “proper” SBS installation anyway.  I tried this virtually with a clean installation of Windows 2000 and ALL updates, so it was a completely vanilla installation with nothing else that could possibly interfere.  So if that’s all you needed then you are done.  If you want to find out what I went through then read on.

Just to re-iterate It did not work, and I tried it 13 times!!!  Please DO NOT follow the steps in this Blog without reading the whole process first!

There are other blogs out there that will tell you that you have to do the SBS2008 installation manually if you want this to succeed.  I was able to get SBS 2008 to join to the domain, transfer all the FSMO roles and it seemed to have a working installation of Exchange 2007 (although because I was doing this virtually and my main aim was to see if I could actually complete the migration I didn’t thoroughly test Exchange) none of the other features that make moving to SBS2008 worthwhile were available.

Sure I had the option of running through the SBS Repair guide and performing all the tasks one by one to repair each and every function of SBS2008 but is it worth it? How long do we think that might have taken?  And would it have ever worked properly once it was done?

Warning Signs!

I should have known from the start when I couldn’t even use Windows 2000 to create the answerfile required to put the SBS2008 installation into Migration mode that I was off to a bad start.  But being as stubborn as I am I persisted, using my Windows 7 host to create the answer by running the SBSAFG.EXE from the SBS DVD.

So I preped my 2000 domain by raising it’s functionality to Native Mode and then run sourcetool.exe from the SBS DVD, the AD preparation ran through OK as I would have expected but it failed to launch the answerfile tool.  Warning sign number 2!!

So I now had my answerfile and I have booted my new VM with the SBS DVD and the answerfile, all seems to go well, it detects the answerfile (as I would expect) runs through the wizard, right up until the last screen when the wizard stops responding and you get the usual would you like to search for a solution online dialogue box.  On I think it was attempt 10 I did try this but it didn’t do me any good!

That was just the beginning!

After the crashed out SBS Migration wizard we are presented with a SBS2008 desktop.  The server isn’t a Domain Controller, no Sharepoint configured; Exchange appears to be installed and looks like it is configurable using the Exchange Management Console.  IIS hasn’t been configured as per an SBS installation, OWA doesn’t work.  And I also cannot get into the SBS Console.

First things first, regardless of all the “broken” items if SBS needs to be a Domain Controller and it MUST hold all 5 FSMO roles along with the Global Catalog role.  To achieve this we need to run DCPROMO.  Select advanced mode and check to install DNS during installation.  You can try this or you can take it from me that it will fail and move on to the next step.

DCPROMO will fail without some intervention.  To make it work run DCPROMO only this time once you have clicked advanced mode and moved to the next screen do the following:

  • Start > Run > CMD <click OK>
  • type CD\WINDOWS\SYSTEM32 <press ENTER>
  • type COPY NTDS.DIT SBSNTDS.DIT <press ENTER>
  • make sure you get “1 file copied”
  • type EXIT <press ENTER>

Now you can complete the DCPROMO wizard.  Once finished and the server has been restarted log back in and transfer the 5 FSMO roles as per: http://support.microsoft.com/kb/324801

You will also need to make the server a Global Catalog server.  To do this open Active Directory Sites and Services, expand the SBS2008 Servername and right click on NTDS Settings, check the box to make it a Global Catalog.

That was the easy bit!!

Now we need to get into the nitty gritty.  If you launch Active Directory Users and Computers you will notice that we are missing the SBS specific Organisation Unit MyBusiness and all its sub OU’s

If you open Group Policy Management Console you will notice that none of the SBS Specific Group Policies exist.

You will also find if you try to run the SBS Console (where EVERYTHING in SBS should be configured) it will also fail to launch.

To repair the SBS Console got Start > Control Panel > Programs and Features, select Small Business Server and click Change.  On the dialog box select Repair (you will need the 2nd SBS DVD)

You will then need to run through each procedure in the SBS Repair Guide which can be found here: http://technet.microsoft.com/en-us/library/dd430085(WS.10).aspx 

Is it worth it??

My opinion NO! Because when you have done this which could take a day or two will it work as it should? I don’t know because after 2 days and 13 failed migration attempts (and believe me I tried everything I could think of, even a repair install of SBS2008 of the top of the failed migration) I decided it wasn’t even worth contemplating.

The way to complete the migration is to either do an in-place upgrade of your Windows 2000 Domain Controller to Windows 2003 or if you would rather not do this install a temporary Windows 2003 or Windows 2008 Server and make this a Domain Controller.

This will allow you to demote the Windows 2000 server, leave your domain in tact and then migrate from Windows 2003 to SBS2008 as per my guide here: https://demazter.wordpress.com/2010/02/12/migrate-windows-2003-with-exchange-to-small-business-server-2008/

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