Upgrade from 2003 Paln


I am a software developer by trade and have been given the task of upgrading our windows 2003 server to windows 2008.

Current here is what is running on the 2003 box:
a. Windows Server 2003 Enterprise Edition service Pack 2
          - Roles
                      - File Server
                      - Application Server
                      - Domain Controller ( Active Directory )
                      - DNS Server
b. Microsoft Exchange 6.5.7638.1
c. Microsoft SQL Server 2008
d. IIS

Basically this box is our only server and acts as a jack of all trades, and unfortunately is to remain this way.

Can anyone tell me, our point me to a resource to explain what i need to do to upgrade this?
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The best advice I can give you is to not get involved in this and hire some help.  As you said, you are a software developer by trade and you recognize that this is a pain to do.

Or better yet, get away from a single box.  The cost of adding a 2nd box is not as dramatic as you might think.  I would assume this is an older server, so you could easily stick with an older server and get an HP DL380 G5 or something similiar and start with 2008 from scratch on that server.  You can then migrate everything else over then rebuild the old server with 2008 and perhaps just use it for SQL.  Or switch to SBS 2008 which with the right licensing can allow you to still have 2 servers.

In the long run this will keep you much more stable as upgrading a server OS can lead to major issues.

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I agree with maytrix as this is not an easy task, nothing like working with a desktop OS and it has the potential for serious downtime that may require a consultant to charge you more to fix it that it would have cost for them to perform the upgrade for you.
that being said, here is some reading to give you an idea of the process:



And this does not cover the Exchange or SQL piece.
Considering your situation, you have no choice but to buy at least one server and virtualize using ESXi or Hyper-v. you dont have any in place upgrade option. If you do so, you will create havoc, no doubt about it. my recommendations would be as follows:

Step1 create a separate virtual server to house SQL, APP and IIS.
step2 create separate virtual server to  house File & Print
Step3 create separate virtual server, join domain, promote as win2k8 secondary DC, transfer all FSMO roles, Make it GC, Keep it as win2k3 native otherwise you will break exchange
Step4 keep that box as Exchange 2003 or virtualize this box or create separate virtual server install exchange, move mailboxes to virtual server

Mind you, you have high risk on virtualizing everything on single Host. However if you can buy at least two servers than you can virtualize these servers with comfort. considering your situation, you may go for Free Hyper-v and FreeNas, even you can configure HA & cluster. I reckon, http://www.dell.com/us/business/p/poweredge-r415/pd would fit into small business.

here is how to for transitioning win2k3 AD to win2k8 AD http://microsoftguru.com.au/2009/08/25/migrate-from-windows-2003-active-directory-to-windows-2008-active-directory-step-by-step/
FSMO Roles http://microsoftguru.com.au/2009/08/05/understanding-fsmo-roles-in-windows-2003-ad-2/

Please talk to professionals/ vendors in your region to find out how they can assist you with the migration. I am sorry there is no easy solution for you.

There is a little add on to step1 & step2, move contents to new VM.
While araberuni's solution is a great one, I suspect cost is the main factor in wanting to do an in place upgrade and adding additional VM's would add to the cost and with 2 physical hosts, that changes licensing requirements, thus adding to the cost some more.

The only low cost solution that should give you a solid end result would be SBS.  SBS includes Windows 2008, SQL and Exchange.  You can also get an add on for it that would allow you to setup a 2nd server which could be the existing server you have once everything is moved to the new one.  

Regardless of what you do, performing an in place upgrade is not a path you should even attempt to go down.  Even someone with vast experience wouldn't want to go down that path.
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Windows Server 2008

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