Transition Windows 2000 Domain To 2008 + Exchange 2003 to 2010

dakarMpower used Ask the Experts™
I've got a Windows 2000 AD environment that needs to be transitioned straight to 2008. In addition, Exchange 2003 is also present and needs to be transitioned to 2010. Can anyone advise on the correct order of operations for this and also of major caveats if any? Here are a few details:

-Primary physical site: PDC (+DHCP, DNS) and (1) BDC (+DNS) and 1 File/Print Server (+WINS)
-Handful of WAN linked physical sites each with (1) site-linked 2000 BDC (+DHCP)
-All Exchange 2003 roles are on one server at the primary site, with no RPC/HTTP access - external access is OWA only

My first consideration is to transition Exchange, then AD. I understand that Exchange 2003 will not run on a domain-functional level of 2008. Can I transition the DCs and leave the functional level at 2000, until the Exchange transition is complete? We may want to leave Exchange 2003 in co-existence for a month or longer to simplify client reconfigurations (many employees are on extended leave).

Another concern is the transition of BDCs at other phsyical sites. Would I complete all work at the primary site, then transition each other controller, making sure to leave the functional level at 2000? I am concerned with the changes to replication topology. As the other sites transition, will they pickup all necessary parameters automatically to continue receiving replication from the newly transitioned primary site ? Any major pitfalls to note ?

Please advise on the best order of operations to complete this, with the significant element of Exchange 2003 needing to be left in co-existence for an extended period. Thanks.

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Thanks for those links Sage, they provide useful instructions. However I'm more concerned at the moment with the correct order to perform these transitions in, particularly with Exchange involved, and with the DCs at other physical locations. Any other comments are helpful as those links don't necessarily address my concerns.
Distinguished Expert 2017

I would think the DC transition should be first.
It is not clear what operational level of AD the exchange 2010 needs/uses.

Do you plan on using newer hardware for the exchange 2010  and at least one DC?
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I believe Exchange 2010 requires at minimum 2000 domain-functional mode, but I have read that Exchange 2003 will not function if the domain functional mode is raised beyond 2003 ? Need to clarify these things.

Another question is whether AD can go straight from 2000 to 2008 or whether you need to step to 2003 first ?

In response to your question, the client wants to virtualize Exch 2010 and new 2008 DCs with VSphere. The hardware will obviously be 64 bit and robust, but I advise against virtualization just because it adds more points of failure.

Distinguished Expert 2017

Depending on the host server capacity, and the type of storage i.e. the storage will be outside the VM.

Make sure that the domain/forest functional level is raised to 2000 native if it is currently mixed.

2000 DC can not exist if the domain functional level is raised above 2000 Native.
2003 DC can not exist if the domain functional level is raised above 2003 Native.

The initial links I posted included ( that the person went through the direct upgrade process from windows 2000 to windows 2008.

The resource allocation to exchange 2010 needs to be well thought out.
Is the storage for exchange be part of the VM or will it be "external" to the VM i.e. iscsi device  such that you could have a cluster/host in waiting. i.e. if the VM fails for whatever reason, you can run the stand-by exchange 2010 after loading in the storage?


Client wants to have the mailbox storage on the Exchange VM.
Distinguished Expert 2017

The MS article discusses what needs to be done to prepare both the exchange 2003 and the AD schema.
IMHO, one should start migrating the simpler thing first.
i.e. the addition of the windows 2008 DC and transition if needed of the AD to a higher functional level, above the windows 2000 native.
Note some features might not be available when the AD is in a lower functional level.
Once this is done. That is when the migration to exchange 2010 should resume.
The overhead with the exchange I/O and Memory needs could outgrow the resources.
Offloading the storage to a dedicated storage if/where available could reduce the overhead and then again it might not.

Are there two Vmware host servers for cluster/failover?


Thanks for this info arnie. There are many other considerations I'm facing but your help is relevant and appreciated.

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