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KB 0000234
Dated 23/04/10
Revision 0.02

Exchange 2003 to 2010 Transition "Swing Migration"


Before we start, I'm aware "Migration", "Swing Migration", and "Transition" have three very
different meanings, Depending on which KB, blog or piece of Microsoft documentation you are
reading. Be under no illusions the terminology, used in the title and the tags on this page is to
catch the web traffic of those, who have an Exchange 2003 Server and want to move all their
Exchange, to Exchange 2010 server.

There are a lot of people who held out on the upgrade to Exchange 2007, and those people
will now be looking to jump straight to Exchange 2010. Unfortunately you can just "Pop in the
DVD" and let it upgrade. In fact there is no direct upgrade, You need to perform what
Microsoft calls a "Transition" to Exchange 2010.

This means you prepare your existing Windows domain and Exchange Organisation, to let
Exchange 2010 exist, then you build an Exchange 2010 server, Migrate your data into it, and
finally remove your original Exchange 2003 server.



In this example I've got a SINGLE existing Exchange 2003 Server running on Windows 2003.
I'm putting in Exchange 2010 onto a new server running Server 2008 R2. Post install the NEW
server will hold client access, mailbox, and hub transport roles.

Step 1 - "Pre-Site Visit"

1. Make sure before you start you have the Exchange 2010 media and unlock code, you don't
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want to download the media on a site with a slow internet connection, (at time of writing the
disk image is 1GB in size).

2. If your existing servers are all x32, and you are also upgrading domain controllers, during
the process you will be extending the domain schema (i.e. it's not 2003 R2) then make sure
you have x32 bit Windows media with you.

3. Make sure any third party anti virus and/or mail scanning software is supported and will
work on Exchange 2010, and you have the media and licences handy.

4. You will need to install on a x64 bit server, make sure you have a server capable, and
Windows x64 bit media with licences.

5. You will need your Exchange 2003 CD, its fond of asking for it during the uninstall process.

6. Before you even think about going further make sure you have a good backup! If you are
lucky enough to have VMware ESX, Hyper-V or another virtualisation platform, consider doing
a P2V conversion on your Exchange 2003 server then simply turning the 2003 Server off, then
if it all goes to hell in a hand cart simply turn the original server back on again.

7. While your thinking about backups - does your backup software support Exchange 2010?
you might need a new Exchange agent, check with your software reseller.

Step 2 - "Pre Install"

1. Before you do anything, it's time for a common sense check, make sure your existing
Exchange 2003 Organisation is happy and running cleanly, and has good communication with
the domain and DNS. Get in the event logs and make sure its a happy server.

Time spent on reconnaissance is seldom wasted!

2. Now you THINK Exchange is happy, it's time to MAKE SURE download the run the
Exchange Best Practice Analyzer (EXBPA). Select "Health Check", and also select Exchange
2007 Readiness check (At time of writing the 2010 option is not there).

3. Make sure your Exchange 2003 server(s) is/are up to "Exchange 2003 Service Pack 2" (In
fact get the latest Exchange update roll up after that as well to be on the safe side).
Build Numbers

Microsoft Exchange Server 2003 6.5.6944 October 2003

Microsoft Exchange Server 2003 SP1 6.5.7226 May 2004
Microsoft Exchange Server 2003 SP2 6.5.7638 October 2005

4. The brief says your Global Catalog server should be at at least Server 2003 SP2, however
I'd be updating all the domain controllers to Service Pack 2. (Note: you need 381Mb free
space on the system drive, plus 170MB additional free space to install SP2).

Locate the Global Catalog Server

Find the Service Pack Level

5. The domain functional level needs to be at "Windows Server 2003". When done, leave
enough time for it to replicate to all domain controllers in the domain.

6. Now the forest functional level needs raising to "Windows Server 2003". When done leave
enough time to replicate across the entire forest.
7. Now you need to put your existing Exchange organisation into "Native Mode".

8. At this point I would apply the "cup of coffee" rule, then check the domain controllers event
logs and the event log on the Exchange 2003 box make sure everything is running smoothly.

9. The new server needs the Office 2007 System Converter Microsoft Filter Pack Installing

Step 3 - "Deploy Exchange 2010"

1. Build your new server apply all the latest service packs and updates. Join it to the domain,
and log in with a user account that is a member of the Schema Admin's group.

2. You need to add certain roles to the new server before attempting to install Exchange 2010
you can script that though I prefer to do things myself. Start > Server Manger > Roles > Add
Roles > Next > Select Web Server (IIS) > Next > Next.
3. On Role Services, under security > tick Basic Authentication > tick Windows Authentication
> Tick Digest Authentication > Under Performance tick Dynamic Content compression.

4. Under Management Tools > Select IIS6 Management Comparability > Next > Install >
Close (when finished).
5. Now you need to add "Server Features", primarily .Net Framework 3.5 that is in Server
Manager > Features > Add Features > Expand .NET Framework 3.5.1 Features > Expand
WCF Activation > tick HTTP Activation > Select to add Required Role Services.

6. Scroll down and below "Remote Server Administration Tools" > Role Administration Tools >
Select "AD DS and AD LDS Tools" > Next > Next > Next > Install > Close (when finished) >
You may be asked to reboot.
7. You need to set the startup type of the "Net Tcp Port Sharing" service to automatic > Click
start > Run > Services.msc {enter} > Locate the Net Tcp Port Sharing Service and set its
startup type to automatic.

8. Put in the Exchange 2010 DVD, run setup.exe, If you are using the multi language version
you should be at "Step 3: Choose Exchange Language option" > Select it. > Select Install
Languages from DVD.
9. Select "Step 4: Install Microsoft Exchange" > Files will extract and setup will Start.

10. At the Introduction screen > Next.

11. Accept the EULA > Next.

12. No, we don't want to do error reporting > Next > Select "Typical" > Next.
13. If this is the only one, or it going to be your main "Bridgehead Server" then it will be
internet facing > tick the box > enter your domain name > Next

14. At this point you select your existing Exchange 2003 Server > Browse to it > Select it >
Next > No we don't want to join the CEIP > Next.
15. Exchange will perform its readiness checks, it will probably give you a couple of warnings,
the first one is telling you (once ran) you can't have an Exchange 2007 server in the domain,
and the other it telling you to replicate free/busy data if you have Outlook 2003 clients. (We
will sort that out later). > Click Install.

16. When done click Finish.

17. The Exchange management console will open, to enter the Product Key, select "Server
Configuration > Select the server > Select Enter Product Key. Then either restart the
exchange information store service or reboot.

Note: You will notice that, if you look in the Exchange 2003 Management Console you now
have an extra administrative group (Called FYDIBOHF23SPDLT - that's geek humour, roll each
letter and number back one).
Step 4 - "Configure and Migrate"

1. Your new server will have one mailbox database and one Public folder database, you can
change their paths, if you want to move them onto faster drives, or other volumes. Select
"Organisation Configuration" > Mailbox > You can right click each data store and move it if
required. Note: You can also set up local continuous replication here as well.

2. Now Its time to make sure nothing is broken, go to the existing Exchange 2003 Server and
check mail flow inbound and outbound.
3. Do you have any clients running Outlook 2003 or earlier? If you do remember the warning
we saw earlier?

If Microsoft Office 2003 is in use, you should replicate the free/busy folder on this server to
every other free/busy server in the organization. This step should be performed once setup

Well now lets assume we do have Outlook 2003, this means calendar scheduling is done from
a public folder (called the SHEDULE+ FREE BUSY folder) this public folder needs to be
replicated to our new server, or calendaring and scheduling will break. Note: If your clients
are Outlook 2007 or above then skip this step - those clients use the auto discover service

On the Exchange 2003 Server Open Exchange Management > Locate the Public folders >
Change the view to "System Folders".

Then expand the "SHEDULE+ FREE BUSY" folder and locate the folder that has the same
name as your OLD administrative group (i.e. NOT the one with FYDIBOHF23SPDLT in it).
right click it and select properties.
Then on the replication tab, add in the NEW Exchange servers "Public Folder Database".

Once you have it added, set the replication.

4. Do you use Public Folders? If not skip to the next step, If you do you will need to replicate
them to the new server, If you have just completed the step above the procedure is the same.
On the Exchange 2003 Server, open Exchange System Manager> Locate the Public folders >
If you cannot see your public folders, change the view to "View Public Folders".
Select each one of your public folders, go to its properties and add in the New Exchange 2010
Server as a replication partner.

5. At this point you need to change the SMTP feed from the old Exchange 2003 box to the new
Exchange 2010 Server, how you do this depends on your network setup, some examples of
how you might do this are,

i. Change the SMTP (TCP Port 25) Port redirect on your router/firewall address
ii. Swap IP addresses from the old to the new server.
iii. Change the translation from public to private IP address to point to the new IP.

Note: If you have any mail scanning servers, anti spam hardware devices etc, then they will
also need changing to point to the new server.

6. Once the SMTP Feed has swapped across, inbound mail may fail and return the following

EX2010.domaina.com #530 5.7.1 Client was not authenticated ##

To fix that you will need to allow anonymous access on the servers default receive connector.
You may also find outbound mail will fail and sit on the outbound queue with the following

A matching connector cannot be found to route the external recipient

To fix that you will need to create a "Send Connector". Launch the Exchange 2010
Management Console > Organization Configuration > Hub Transport > Send Connectors >
New Send Connector.

Give the new connector a name > Under "Select intended use for this send connector", select
"Internet" > Add >Set the address space to a single asterisk > Select "Include all sub
domains" > OK > Next > Enter a smart host (if you use one) > Next > Next > New > Finish.
Then test mail flow works once again, this time through the new server.

7. Now you can start moving mailboxes from the old server to the new one, what I tend to do
is move one mailbox, test mail flow outbound/inbound, then test mail flow internally from the
mailbox I've just moved, to a mailboxes that's still on the old server. Once I've proved this
works I will move the rest of the mailbox's.

To move a mailbox, open the exchange 2010 management console, expand "Recipient
Configuration" > Select Mailbox > You should see all the mailbox's listed > Right click the
mailbox you want to move > Select "New Local Move Request".
At the introduction screen, hit the browse button and select your new servers data store >
Next > Next > New > Finish.

Once you have moved one and tested, it you can move the rest of the mailbox's.

8. Next task is to change the server responsible for generating the offline address book. On
the Exchange 2010 server Exchange Management Console, Expand "Organization
Configuration" > Mailbox > Select the "Offline Address Book" tab > Right click the Default
Offline address book and select "Move" > Browse > Select the new server > OK > Move >
9. The old Exchange server relies on the recipient update service, the new server does not. If
you try and edit your address policy with the Exchange 2010 console you will see this error,

"The specified e-mail address policy couldn't be edited. E-mail address policies created with
legacy versions of Exchange must be upgraded using the 'Set-EmailAddressPolicy' task, with
the Exchange 2010 Recipient Filter specified."

Unfortunately this can not be fixed in the management console, you need to issue some
powershell commands to fix it. Click Start > All Programs > Microsoft Exchange Server 2010
> Exchange Management Shell.

Issue the following command,

Once executed you need to press "Y" to accept.

Note: You may have multiple recipient policies in operation, they will all need upgrading.

10. While we still have the "Management Shell" window open we need to update our "Address
Lists" as well to do that issue the following 5 commands one by one.

Enter "Y" for yes when prompted.

Step 5 - "Do Nothing"

Seriously, now you need to wait, before you can proceed all the public folders need to have
replicated to the new server, in some cases this can take days, as a general rule of thumb, at
this point I would wait 1 week before proceeding to decommission the Exchange 2003 server,
this allows for both public folder replication, and any head slapping "Doh! we forgot to {insert
random forgotten thing here}".

Also in this time, any clients running Outlook (Pre 2007) can log in, and will get their Outlook
profile automatically updated to point to the migrated mailbox on the new Exchange 2010
Step 6 - "Decommission and remove Exchange 2003"

1. Lets check our public folders, this one is in sync.

And then switch to system folders (See here if you forgot how to swap the view). If you see
the status as "Local Modified" or "Remote Modified" then check the item count on the folders
to make sure they have the same item count (Select the status column).

2. Once you are happy you can remove the replica that is on the Exchange 2003, > Properties
> Replication > Select the 2003 Server > Remove > Apply.
3. Repeat the above procedure for all the public folders you have set to replicate to the new

4. Remember when you installed Exchange 2010 it created a new administrative group in your
Exchange 2003 organisation? (The FYDIBOHF23SPDLT one). It did this to connect to the
existing organisation, and it created some routing group connectors, you now need to remove

5. Even though Exchange 2010 does not use the recipient update service, you need to tell
Exchange 2003 that it does, because you can't uninstall Exchange 2003 from a server that
thinks it is providing this service. Launch the "Exchange System Manager" > Expand recipients
> Select Recipient Update Services > Right click each one and change the server name to the
new Exchange 2010 server. Do this for EVERY policy.
6. We are now going to start deleting things, have a quick common sense check! Are you sure
everything is OUT of your Exchange 2003 Databases? If so, delete your stores from Exchange
2003 > you will need to dismount them first > Repeat for all private databases.

7. Finally you can now go to "Add or Remove Programs" and remove Exchange 2003.
(Change the action type to "Remove"). Note: You may be asked to insert the Exchange 2003
install media.
When done reboot the server.

Step 7 - "Finish up"

1. Now you may need to change your backups to include the new datastores.

2. If you have any links to "Outlook Web Access" (i.e. on your public website or in Sharepoint,
they will need the URL's changing from https://server/exchange to https://server/owa

3. You may get some support calls like "internal user A cannot send an email to internal user
B" if that happens check that they are NOT using the automatically remembered email facility
in Outlook, this stores previously typed email addresses in a local file called an NK2 file (or
nicknames file). but it stores internal addresses like this...

Those paths no longer exist, get then to pick the name from the "Global Address List" instead,
or if they are really persistant you can add a line to the login script that deletes the .nk2 file.

Update 26/05/10

Thanks to Rick Faria, Who both pulled me up on my shoddy technical terminology, and asked,

The only thing I don't see in your article and actually the thing that seems to be the most
involved is dealing with trying to move over your Exchange 2003 SSL cert for OWA or if your
renewal is close taking care of that with a new one. You don't really mention that process.

Fair enough, here we go,

Transferring Certificates from Exchange 2003/2007 to Exchange 2010

If this helped in anyway let me know . To get me in to do this for you would have cost you a
fair few thousand pounds, feel free to make a donation.

If anyone has anything to add, click here.

References - Credits - Or External Links

Automated prerequisite installation via PowerShell for Exchange Server 2010 on Windows
Server 2008 R2

Address List and EAP filter upgrades with Exchange Server 2007

Thanks to Rasmus Haslund for the Feedback.

PeteNetLive ©2010

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