Moving from server 2003 to server 2008

Wilf used Ask the Experts™
I am in the process of moving a server from Windows server 2003 standard to windows server 2008 standard

I have ran the 32 bit adprep on the server 2003

I have backed up system state backup and user profiles using the backup function in windows server 2003.  They will be in one backupfile
The profiles are not on C drive, but are on F data drive on the server
Once I have installed server 2008 on the server, do I just restore the file created with the backup including state backup and the profile files?  Does this restore all users to their original 2003 profiles and permissions on the 2008 server?  Users could then log on, and all will be the same for them?
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Is this server Domain Controller? and are you going to put the new server as Domain controller?
Also you should not restore system state of windows 2003 on windows 2008.

as the user data is on D drive so  leave D drive and just install windows 2008 on c drive.
Lee W, MVPTechnology and Business Process Advisor
Most Valuable Expert 2013

Allow me to apologize in advance - I'm going to be somewhat blunt and possibly sound harsh - I do not mean to suggest you don't have the capability to learn this and be very successful at it... I'm sure you do.  But if it's not your primary job responsibility and not something you expect to do reasonably frequently, you should have it done by an expert or you should go through appropriate training to learn it - which would cost more than hiring the expert (which is why if you go through training, it should be because you expect to do this often).

You've never done this before and you're doing with your LIVE server?  Unwise in my opinion.  You need to do this AT LEAST ONCE in a test environment so you can experience how it's done and have a good idea for doing it with your production network.

Even with the information provided to you here, you should be TESTING first in a test environment to make sure you understand whatever we've said and to see what you might be expecting.

Or hire an experienced professional... $500-1000 in consulting services is a LOT cheaper than DAYS being down because this gets messed up.  Consider it insurance.

Now, assuming you're going to take this advice and setup a test server at least, here's the high-level overview of the procedure I'd use

You CANNOT backup a 2003 server, install 2008 to same physical server, and restore the user accounts and system state to that same server*

*Certain exceptions to the technical definition of some of those words and phrases if you have more than one domain controller already but as a general rule, in way you're describing and I'm reading, you cannot.

ALWAYS perform a backup first.  

Install a new PHYSICAL server if you can.  If you simply cannot, then you should be installing virtually (actually, I would ONLY install virtually nowadays.  If your existing server were virtual, this would be a lot simpler to do on the one system).  If you want to preserve your users and user profiles AND install to the same physical server, you need to perform a swing migration.  Even then, preserving the profiles is not as easy.  A swing migration is were you install a server TEMPORARILY, moving to the temporary system on another server, so that you preserve the domain and then you can wipe the physical server and migrate a SECOND time to the old physical server.

Like I said, I would only install virtually at this point because, though there would be a relatively minor performance hit, the flexibility for growth and capability is EASILY worth the performance hit.

So, again, if you're reading the above and the below and are not comfortable with 80%-90% of what I'm saying based solely on the description I've given, then as a professional who fixes messes created by inexperienced "office computer guys" trying this on their own, I would STRONGLY recommend you hire someone to do it right or get appropriate training first (BOOKS have been written on this and we are simply not going to do you or the content justice in a question here). Now, the high-level overview of what I would do:

1. backup the existing server.
2. Install a virtualization product on another system (ESXi or Hyper-V would be my choice; I use Hyper-V primarily).  
3. Install another virtual system with Server 2008 and join it to the existing domain.
4. Run DCDIAG /C /E /V on the existing 2003 DC and correct any unexplained errors - a successful migration requires a healthy Active Directory.
5. Run ADPREP on the existing server to prepare the domain for the introduction of a 2008 DC
6. Run DCPROMO on the 2008 Virtual Machine (VM) and make it a DC in your domain.
7. Migrate your data and everything else (databases, DHCP, etc) to the VM from the 2003 server.
8. Run DCPROMO on the 2003 server to demote it so that it is no longer a DC.
9. Wipe the existing server and install your virtualization product on the existing hardware.
10. Move the virtual machine from the temporary system to the newly rebuilt old server.

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