How to transition from SBS 2003 to Windows 2008 Standard?

Hi,

I'm preparing to migrate from a Windows 2003 SBS with Exchange 2003 and SQL Server 2000 to a Windows 2008 Standard machine with Exchange 2010 Standard.

I'd like to keep the 2003 SBS machine up running SQL 2000 for a few months after transitioning the DC to the Windows 2008 box and Exchange 2003 to 2010. Is this possible? Will SBS 2003 allow me to move over to the Windows 2008 as a Domain Controller? What's the procedure to do so?
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PaulELSAsked:
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Rob WilliamsCommented:
demazter's has written an excellent article on moving from SBS 2003 to Server 2008 and Exchange 2010. See the following link:
http://demazter.wordpress.com/2010/04/29/migrate-small-business-server-2003-to-exchange-2010-and-windows-2008-r2/

This migration works well, but you cannot maintain the SBS in this configuration. SBS must maintain the 5 FSMO roles. You could add a Windows 2008 R2 server as a domain controller to your existing SBS 2003 domain and do the migration at a later date if you like. As per the following:

Add an additional server to an existing SBS 2003 domain:
If the new server is a newer version such as server 2003 R2 or server 2008 you first need to run adprep, on the SBS, from the new server CD set to "extend the SBS schema".
If the new server is server 2003 R2adprep  it is located on the second CD under \CMPNENTS\R2\ADPREP\
If Server 2008 see: http://www.petri.co.il/windows-server-2008-adprep.htm

-Make sure the SBS is fully up to date with all patches and service packs, which makes it more compatible with the new O/S's (2008, Vista, Win7)
-You need to create a computer account for the new server, on the SBS, using the wizard located under server computers in the server management console of the SBS
-If the new server has more than one NIC, disable all but one while joining the domain. Once completed you can enable others
-Then point the new servers DNS only to the SBS, and join the domain using the wizard  http://SBSname/connectcomputer
-If the new server will not join with connectcomputer (I don't believe 2008 will yet), add it manually under My computer properties / computer name / change, and then in Active Directory move the computer from the Servers OU to the MyBusiness/SBS servers OU
-If you wish the new server to be a domain controller, now you can run DCpromo on the new server. You must use integrated zones when working with SBS. (there are different options in the wizard, just choose defaults and integrated). I would recommend at the same time installing DNS.
-If the server is going to be a terminal server (DC and TS is not recommended) you can add the Terminal Server and TS Licensing Server roles now.

You may want to review the following as well:
Add and Manage Additional Servers in a Windows Small Business Server Domain
http://www.microsoft.com/downloads/details.aspx?FamilyID=6f4015f2-7606-4eaa-828a-00b8df6bd999&displaylang=en
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PaulELSAuthor Commented:
Hi RobWill,

Thanks for the insight. So to clarify, I would be able to maintain the SBS and Windows 2008 Standard server in the domain until the 5 FSMO roles are transferred? So long as the Windows 2003 SBS machine has the 5 FSMO roles, they will coexist peacefully?

I've read that Windows SBS will shut itself down once an hour in some circumstances where there are other DCs on the network. How do I avoid that?
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Rob WilliamsCommented:
You can add as many DC's or member servers as you like to an SBS domain for as long as you like with no issues whatsoever.. That is a common misconception. What you cannot do is add another SBS to an existing SBS domain. If you do that, one or the other will start shutting itself down after 7 days. In a migration scenario there is a hotfix that will extend that to 21 days, but that is all.

If you transfer the FSMO roles to another server the same restrictions apply. The SBS will start shutting down after 7 days.
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LindsayColeCommented:
If you are looking to transition out of SBS2003 due to simply outgrowing it's user limit, I recommend a Swing Migration. I performed my first with the documentation from: http://www.sbsmigration.com/.

It isn't free, but the peace of mind is amazing for your first swing. Jeff Middleton is a great guy, who knows his stuff.
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PaulELSAuthor Commented:
I've begun the migration. Working on Exchange now.
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PaulELSAuthor Commented:
There seems to be an issue with e-mails being transmitted between exchange 2003 and exchange 2010 during the coexisting period. On EX 2010, my queue to the 2003 instance is filling up. I see that Exchange 2003's virtual SMTP connector shows a bunch of connections from the 2010 server, however none of the e-mails are making it through.

Looking at the Exchange 2003 SMTP logs, I see timeout waiting to connect entries:

2010-11-17 18:03:54 192.168.22.23 OutboundConnectionResponse SMTPSVC1 EX2003Machine - 25 - - 451+4.7.0+Timeout+waiting+for+client+input 0 0 42 0 301000 SMTP - - - -
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Rob WilliamsCommented:
Sorry PaulELS, I am not familiar with that issue. You might be best to post that in a separate question.
--Rob
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