Please critique my 2003 to 2008 upgrade plan

thedude0901 used Ask the Experts™

My company has finally approved the budget to do a complete back end upgrade from 2003 to 2008.  As I've never done anything like this before I was hoping to get some input on the general plan and problems that may be encountered.

The environment consists of the following:
16 Windows 2003 Standard Edition 32 bit SP2 servers with about a 50/50 mix of 2003 and R2.
1 x Exchange 2003 Enterprise Edition with 60 mailboxes
2 x AD servers with DNS (AD integrated), DHCP, and Time services
The remainder are various file, print, web and application servers.
The workstations are a mixture of XP 32 bit and Windows 7 64 bit.
The active directory functional level is 2003 native.

The plan is to upgrade everything to 2008 R2 64 bit and upgrade Exchange 2003 to 2010.  All of the servers will be upgraded to new hardware with 2008 R2 and the applications/data will be moved to it.  The old hardware will be retired or retasked for other things.

I'm quite experienced and comfortable with 2003 but 2008 is a new animal.

Here are the general steps I believe will be necessary.  Please comment.

1.  Build out two new AD controllers (AD1 and AD2) and add to the domain.
2.  Move FSMO roles from old 2003 server (DC1)  to new 2008 server (AD1)
3.  Change DHCP to have DNS point to new AD1 and AD2 servers
4.  Reboot all workstations and update existing servers to verify new DNS information.
5.  Stop DHCP on old DC1 and DC2 servers.
6.  Start DHCP on new AD1 and AD2 servers.
7.  Reboot workstations again to get new addresses from new DHCP servers.
8.  DCPROMO old DC1 and DC2 and shut down servers.  Hardware to be retired.
9.  Reboot Exchange server to make happy with new domain controllers and DNS location.
10. Drink heavily.

11. Migrate existing file/print/application servers one at a time from 2003 to 2008 R2.
12. Retire old hardware.
13. Drink heavily.

14. Build new server and add to the domain.
15. Install Exchange 2010
           Please note:  This is where i'm a little confused.  Can I install 2010 on to a 2003 domain then raise the functional level to 2008 later?
16. Move mailboxes from old 2003 to new 2010 server.
17. Uninstall the 2003 server.
18. Remove the old server from the domain and shutdown box for good.  Retire the hardware.

19.  Raise the functional level of the domain from 2003 to 2008.

I'm pretty comfortable with everything except the Exchange part.  I've done plenty of migrations but they've always been in the same version.  A double jump with a domain and exchange version makes me nervous.  Any thoughts?

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DRINK HEAVILY before starting the Exchange Migration ... ROFL ... Looks like you have the bases covered, I'd add one step prior to any of the sequences you have listed -- GOOD BACKUP PRIOR TO MIGRATION OF OLD SERVERS AND BEFORE SHUTTING DOWN - just in case - you never know ...
The exchange migration to 2010 is actually really easy, far better than 2003 to 2003

there are two ways, buth have pros and cons

OPTION 1 = use the exch 2010 management console and the "Move Mailbox" command

This option is really slick, start it running, and the majority of the process runs in the background
the only bad side is that the moved mailboxes will be "Legacy Mailboxes" which can be a pain to deal with in certain areas,
We ran into a problem when trying to reconnect a edb file and found that the new mailboxes picked up straight away, but the legacy ones caused me a bit of hassle

OPTION 2 = export and import method

This is probably the best option, new server, new mailbox
Get your users to prep their mailboxes for the change, by this i mean, emptying deleted items, junk items, general inbox crap, etc
Export each mailbox to a pst file
Import into the new exchange box

You Choose....
0. Run adprep to add Windows2008-specific attributes to your schema so that you can have win2K8 DCs

5,6.  There is actually a way to move the DHCP database.  MS has a good KB with instructions:

7,9   IMO, not really necessary,  But, if you feel the need, feel free (I wouldn't reboot an Exchange server unless it was necessary, or to install an update.  For Exchange, just make sure its network settings use the 2 new DCs for DNS, and you should be good to go)

11.  Good luck with that.  Hope you don't have any legacy/custom applications that won't run in a 64bit environment.

15.  The answer to your question is Yes

15.  You didn't let us know how prepared you are for Exchange 2010.  Here's some good reading material:

Good luck.
Qlemo"Batchelor", Developer and EE Topic Advisor
Top Expert 2015

This question has been classified as abandoned and is being closed as part of the Cleanup Program.  See my comment at the end of the question for more details.

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