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Assistance require for Exchange 2003 to 2010 migration

Hi all

I need to do a migration from our Server 2003 Standard (SP2) / Exchange 2003 Standard (SP2) to a new Server 2008 R2 (SP1) / Exchange 2010 Standard box.

I've got the 2k8 R2 server up-to-date with Online Updates, but haven't installed Exchange 2010 yet as I do know really know where to go from here.

A lot of what I've read so far conflicts in the order of things to do...

So far, I have:

(on the 2k8 box)
1.  Installed .Net Framework 3.5 sp1 and the default IIS config.
2.  Used the powershell to run
Import-Module ServerManager

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, then
Add-WindowsFeature NET-Framework,RSAT-ADDS,Web-Server,Web-Basic-Auth,Web-Windows-Auth,Web-Metabase,Web-Net-Ext,Web-Lgcy-Mgmt-Console,WAS-Process-Model,RSAT-Web-Server,Web-ISAPI-Ext,Web-Digest-Auth,Web-Dyn-Compression,NET-HTTP-Activation,Web-Asp-Net,Web-Client-Auth,Web-Dir-Browsing,Web-Http-Errors,Web-Http-Logging,Web-Http-Redirect,Web-Http-Tracing,Web-ISAPI-Filter,Web-Request-Monitor,Web-Static-Content,Web-WMI,RPC-Over-HTTP-Proxy -Restart

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(on the 2k3 box)
1.  changed the Exchange instance to "Native Mode"
2.  raised the AD Forest to 2003

Where to from here?

For information's sake, our Exchange 2003 server is Public facing.  Is the ONLY Exchange server and is (obviously) the current Domain parent for our internet domain.
I want the new Exchange server to be the same as the old so I can get rid of the old.  They can coexist if need be, but I need to note that the 2003 box is above the 75GB store limit and keeps dismounting.
Reece Dodds
Reece Dodds
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4 Solutions
MASTechnical Department HeadCommented:
Reece DoddsAuthor Commented:
I've actually read a lot of the exchangegeek pdf before, but where I'm confused is that you can't rename an exchange 2010 server, and you can't use dcpromo.exe

How does this work when I need it to have the same name as the 2003 box and take it's place as domain parent?
MASTechnical Department HeadCommented:
You mean you want to give the same name of exchange2003 server to exchange 2010?

If yes please explain why

What exchange2010 installation got to do with DCPROMO?

Awaiting your reply
Making Bulk Changes to Active Directory

Watch this video to see how easy it is to make mass changes to Active Directory from an external text file without using complicated scripts.

Once you install Exchange server on member server, promotion of that server to directory server is not supported

Also if you installed Exchange on DC server role, then demotion of DC is also not supported


Also you cannot change organization  name that is already set with Exchange 2003
Its not recommended to install Exchange on server that is also acting as DC unless you are using SBS server

To do what you are trying to do, install 2010 on member server 1st in existing exchange Organization,
then do mailbox migration, lastly decommission 2003 Exchange server completely, demote  if same machine is domain controller also and then install new exchange 2010 member server with the old name as that I think you are intersted

According to me Exchange server hostname  is never dependency for any application and you do not need to maintain old host names

Straight from Microsoft: Exchange Server Deployment Assistant
Arjun VyavahareTechnical ConsultantCommented:

Refer this video in which each and every steps are available:
Reece DoddsAuthor Commented:
Sorry for the no reply - I'm in Au so the time zone screws things up.

Our existing Exchange 2003 server (which I inherited the management of) seems to be a AD DC and DNS server as well as an Exchange server.   But, it is the ONLY box on that domain, and is a public facing mail server (not front end).  The client PC's (wherever they are in the world) can be connected to any domain they wish, or none at all and they just configure their outlook to connect to "mail.ourwebsitedomain.org.au".  Which I think is RPC-HTTP.

I want our new Exchange server to replace this server in it's entirety and still function the same for the client PC's.

Are you telling me I don't need to setup AD DC or DNS on the new server for it to be accessible by "mail.ourwebsitedomain.org.au"?

In our domain's zone file, I have the MX records for the "ourwebsitedomain.org.au" and A records for mail pointing to the Exchange server's public IP...
I would do this in stages, first I'd install a windows 2008 member server and migrate from exchange 2003 to exchange 2010 on that box.  Once that is migrated and verified 100%. Remove exchange 2003 from the Windows 2003 Server.  See the link I gave you before.

Then install another Windows server 2008 as a member server, then dcpromo it to the new domain controller.  After 100% working dcpromo the windows 2003 to member server then remove from domain and power off.
I am not aware that you are having single 2003 Domain controller
Before installing Exchange on new member server modify AD schema to 2008 R2 with adprep \ adprep32 utility that will found in 2008 R2 DVD (You need to run ADPREP on 2003 DC server and if it is 32 bit you need to run adprep32) , then you install 2008 R2 member server and promote it to 2008 R2 ADC, then check if AD replication is working properly.


Once you done that you can introduce another 2008 R2 member server, install 2010 SP3 in co-existence, do mailbox migration, migrate public folders etc and then finally uninstall Exchange 2003 from 2003 DC and once that done successfully, you can use 2003 DC if wanted to or you can simply decommission that by transferring FSMO roles to 2008 R2 DC

MASTechnical Department HeadCommented:
As suggested above I would suggest the same. Below are the brief steps
1. Install a new Ad. domain controller 2008
2. Transfer all the roles to the new DC.
3. Then install exchange2010 on another box with 2008 using the above links provided.
4. Transfer your PF and mailboxes to the exchange2010 server.
5. Keep your exchange 2003 running till everyone login to outlook at-least once.
6. Then monitor for few days for any errors. if all ok decommission exchange2003

7. Keep the old 20003 server as Additional domain as you need minimum 2 DCs in your org (but you can use ADC for some other app as well e.g. fileserver, DHCP, WSUS, etc.)
Reece DoddsAuthor Commented:
So if I understand you correctly, I need two 2k8r2 servers...
One to take all the AD DC roles from the 2k3 box, the other for the Exchange 2010 (because you cant dcpromo once Exchange is installed)?

How does this help me get the new public facing exchange server configured as mail.ourwebsitedomain.org.au?

I don't want two 2k8r2 boxes running.  The server is ONLY used for Exchange... there is no other domain control needed.  This is all done by a local domain controller on the private side of our firewall.

Sorry for the 1001 questions, I want to make sure I take the best approach for our scenario before making any irreversible and possibly harmful changes to the 2k3 box.   Is there a way I can take a backup of the Store and Configuration so I can revert if something goes wrong?  (other than imaging the HDD/partition)
You say you have a domain controller on the internal network?  is that domain name different than the one the exchange is currently on?

Sounds like what you need  is this kind of setup.

Internal domain(private)
Internal mail server running transport & cas roles

Exchange Edge server running in the DMZ

 Unless that public facing server is an SBS server I can't see how you/they got exchange to run on it.  Unless 2003 wasn't so picky.

Exchange MUST belong to an domain, NO IF's, AND's, or BUT's
Reece DoddsAuthor Commented:
Yeah, the internal domain is different.  Our exchange server sits on the public side because we have a number of other offices and remote workers on the same email domain without exchange servers in their offices or at home that use Outlook via RPC-HTTP to synchronise mail.

For a number of reasons, I want to avoid a front-end/back-end server situation, the primary being that we will soon be migrating to Hosted Exchange (probably O365 E3).

So a lot of recommendations are to avoid the Exchange 2010 box being the DC primary.
So I'm happy to make it a member server of the 2003 domain and migrate the Exchange from 2003 to 2010 and leave the 2003 DC on the network, but don't I HAVE to have the public facing mail server named correctly for the clients to be able to connect without reconfiguration (ie. "mail.ourwebsitedomain.org.au")???

Can I rename the 2003 exchange server to something else with the assistance of http://www.microsoft.com/en-us/download/details.aspx?id=4132 (eg. ex2k3.ourwebsitedomain.org.au), and have the 2010 box named correctly and join it as a member, migrate mail transport roles in one session?

Or will renaming the 2003 box break exchange so I can't move anything across to 2010?
You should not rename 2003 Exchange, its risky and not advisable

You already now aware that its not best practise to install Exchange on DC, there are many known issues you need to take care of.

Your scenario:
You have single ADDC with Exchange 2003 installed and same time this is published on internet as well
Now you want to replace it with 2008 R2 server with Exchange 2010

For your scenario, 2 windows 2008 R2 servers are ideal actually (1 as ADC and one as Exchange 2010)
i don't see any issue to publish 2008 server Exchange box on internet directly with required name space for RPC-Https or for OWA
You need to point your MX to 2008 R2 and also same time you need to point your OWA with 2008 exchange server. (I assumed that MBX, CAS and HUB servers all roles are installed on single server
You must take care of legacy exchange 2003 url and SAN certificates.

For what so ever reason if you don't want to put-up 2 windows 2008 Servers, you can have below approach even though I do not recommend

Install new 2008 R2 member server
Promote it to ADC
Install Exchange 2010 on that box in co-existence
rest of the process is same
In either case you have to have one ADC on 2008 R2 box.
note that now you cannot remove active directory from 2008 R2 server as it will break Exchange

Once you demoted exchange 2003, its your decision weather to keep DC on 2003 or not

When you say this Windows 2003 server is public facing, do you mean that the IP address of the Windows 2003 server is your public IP?  Or is it behind a firewall and has a private ip scheme?
Reece DoddsAuthor Commented:
@ktaczala - we have a number of public IP's in a range for various uses...  Our 2003 exchange box is one of them.  It's on the public side of our juniper firewall (don't worry though, it's not a DMZ, there is only specific set of ports open purely for mail transport).

OK, so I've now added one of our other 2k8r2 servers to the 2003 domain.
Do I now need to install AD services on it so I can transfer FSMO roles to it eventually?
If I join the Exchange 2010 (2k8r2) box to the domain as well, how can I configure Exchange so that it can operate in co-existence and become the main email server?  Do I have to have the server named "mail.ourwebsitedomain.org.au" for it to be accessible by user's Outlook via RPC-HTTP and OWA?  If so, that poses a problem because the 2003 box will be named the same and they will clash...
So, now you have decided to use two 2008 R2 servers..


Yes, you need to promote 1st box to ADC and then check replication is working across 2k3 and 2008 R2 Box and then you can transfer FSMO roles

But question - Do you give new 2008 r2 DC also Public IP since your Exchange 2K3 box has public IP address ?

 You need to get new SAN certificate that include, mail.emaldomain.org, legacy.emaildomain.org (This needs to be used for 2k3 server) and autodiscover.emaildomain.org

Also you need to set Exchange 2k3 url to legacy.emaildomain.org and allow users to connect through mail.yourdomain.org (OWA address) so that if mailbox resides on 2K3 server, users will be automatically redirected to 2K3 server
There is PowerShell command to run from 2010 server who takes care of that redirection

The same OWA URL can be used for Outlook Anywhere (RPC-HTTPS)

Once your internal mail flow started working properly between 2K3 and 2010, you need to point your MX records to new Exchange 2010 server and also you need to delete SMTP connector on 2K3 server and need to create new Send Connector on 2K10 server

Technically, how to do this is well documented in MAS's 1st comment links or you will get number of links on internet to achieve this

Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
So, there is pretty clear documentation for what you are trying to do:

You'll stay out of trouble if you follow that exactly.

Installing this as an additional server will allow you to create another mail database in which you can move some of your mailboxes in order to lessen the load on the existing Exchange 2003.  Moving mailboxes will be transparent to users for the most part.

Reece DoddsAuthor Commented:
sorry for the slow follow-up on this question.  I have the 2003 system running stable again for the moment and have put my migration on hold until I can image the existing system in case I 'eff' it up during the migration to 2010.

thanks for you suggestions so far - and your patience as well.

Reece DoddsAuthor Commented:
Thanks to all those who helped on this question.  I ended up going straight from Exchange 2003 to Exchange Online (via O365).  There was no in-between steps required and I used the built-in Exchange migration wizard that Office365 provides.  Both servers co-existed while I did the mailboxes in batches over a period of a month.
We're full Exchange Online now though and I've done 3 other migrations to the same O365 tenant since.

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