Migrating (best practices)

I am planning out my first server migration, I am moving from Windows Server 2003 to 2008. I cant go to R2 because our accounting software will not play nice with R2 without a pricey upgrade that only offers compatibility with R2 (and nothing else). The same goes for 2012, its not officially supported according to the software vendor.

The server handles DNS, DHCP and the Domain Controller roles. It is also used for the accounting software which is based on Pervasive SQL. It does not function as a print server, share drive, IIS, exchange, etc...

I have verified the hardware meets recommended system req's for 2008. I have read the technet on this subject (Guide for Upgrading to Windows Server 2008) but would like to create a duplicate or clone of this server and test out the migration a few times before I make a permanent move.

How can I do this? I have access to the VM suite through my school, so if there is a tool in their that can help with the cloning please let me know. Any other tips or advice? I've been drawing up plans for 2 weeks, but no matter how much planning/reading I do I just don't know if I am doing this right since its my first time and this is the server for the business.

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Comments

LarryDaMan

Not a server guy, so good luck. But, I am a bit of a grammar Natzi and you constantly mix up "there and their" in your posts. I am probably a dick for pointing this out, but I come in peace.

One day it might matter (resume/technical writing/official e-mails).

--chris--

LarryDaMan wrote: »

Not a server guy, so good luck. But, I am a bit of a grammar Natzi and you constantly mix up "there and their" in your posts. I am probably a dick for pointing this out, but I come in peace. One day it might matter (resume/technical writing/official e-mails).

No, I appreciate it. The bad part is, I often go back and flip/flop on which there/their I should use. I probably had it right lol.

edit: It should be "...so if there is a tool in there that..." correct?

edit 2: The reason I came back to post:

In M$ TN, the link I posted above it states:

Be aware that you cannot uninstall Windows Server 2008. After the upgrade is complete, you cannot uninstall Windows Server 2008. However, if Setup fails during the upgrade, you can roll back to your previous operating system.

But in the same TN article I have also found this:

Installs the new operating system side-by-side with the older operating system, enabling you to roll back to the older system if there is a problem.

So what circumstances must occur in order for the upgrade to roll back? Can I roll back any upgrade if the results are detrimental?

GAngel

MS has a server migration tool. I've never run it on a non R2 system but for test purposes it should tell you all the major pitfalls.

Windows Server Migration Tools and Guides

LeifAlire

Is the server physical or virtual, I would first bring up a new server and make it a DC then transfer the FSMO roles over to the new server along with enabling DNS and DHCP roles, also check to see if you can bring up another server to have a DC running another software (Pervasive SQL) is not a good idea.

rsutton

It sounds like you are talking about doing an in-place upgrade. In most migration scenarios this is not supported. The Method I normally use for these migrations is:
-Built a brand new server with Server 2008
-Raise the Forest/domain functional levels to 2003+
-Dcpromo the server as an additional Domain Controller
-Verify AD & DNS replication
-Transfer FSMO roles to the 2008 server
-Update DHCP scope with new DNS server
-Update any statically assigned servers with new DNS server
-Dcpromo the 2003 server
-Check DNS to ensure that there are no references to the 2003 DC
-Decomission the 2003 box

RomBUS

rsutton wrote: »

It sounds like you are talking about doing an in-place upgrade. In most migration scenarios this is not supported. The Method I normally use for these migrations is:
-Built a brand new server with Server 2008
-Raise the Forest/domain functional levels to 2003+
-Dcpromo the server as an additional Domain Controller
-Verify AD & DNS replication
-Transfer FSMO roles to the 2008 server
-Update DHCP scope with new DNS server
-Update any statically assigned servers with new DNS server
-Dcpromo the 2003 server
-Check DNS to ensure that there are no references to the 2003 DC
-Decomission the 2003 box

Perfect. Quickest way

--chris--

rsutton wrote: »

It sounds like you are talking about doing an in-place upgrade. In most migration scenarios this is not supported. The Method I normally use for these migrations is:
-Built a brand new server with Server 2008
-Raise the Forest/domain functional levels to 2003+
-Dcpromo the server as an additional Domain Controller
-Verify AD & DNS replication
-Transfer FSMO roles to the 2008 server
-Update DHCP scope with new DNS server
-Update any statically assigned servers with new DNS server
-Dcpromo the 2003 server
-Check DNS to ensure that there are no references to the 2003 DC
-Decomission the 2003 box

Thank you for this list. I only work here one day a week, and thats all the time I get so I have to put out urgent fires first and as I get time I work on the server stuff.

Ill start by figuring out what hardware we are currently using on this server, attempt to find an affordable clone/build it and move on from there. I'm sure Ill be back soon enough with more questions

--chris--

New plan....will this work?

Keep the current server running, its only 2 years old and has plenty of hardware "oomph" to run the accounting software.

Pick up a new server and use that as the primary DNS, DHCP, Domain Controller, etc....and keep the old server on the domain just to serve the files needed for the accounting software. I would use Server 2012 on the new server, and keep the server 2003 running as well but reomve all of its duties aside from the accounting software. I have not started to research this idea, but it sounds logical.

This should work right?