Moving from Exchange Server 2003 to Exchange Server 2010

I recently had the opportunity to migrate an Exchange Server from 2003 to 2010 and for the most part it was very straight forward but I encountered a couple of gotcha’s that I thought I’d share.

In preparing for the migration I read up on the differences between the two systems. I strongly recommend reading these documents, these authors really did helped us all in putting the pieces together:

Exchange Server 2007 Turbo Transition Guide – I found this document very helpful, especially when talking about certificates. Paul did a great job in detailing the steps involved. Although the environment he was working in wasn’t exactly like mine, it was a very helpful guide.

Rapid Transition Guide From Exchange 2003 to Exchange 2010 – this is a great guide to the basic steps involved in moving from 2003 to 2010, Milind did an great job with this and links to all of the reference material you’ll need to gain a thorough understanding of the topics discussed.

Public Folders

Moving public folders didn’t go so well for me. Even after following the guides and Googlin’ until all hours of the morning(s), replication would not work. Even though, after checking permissions, services, and everything else I could think of, I found no issues. What I ended up doing is a forklift-type operation… very sneaky! Here’s how I got around the replication issue:

1) With my mailbox on Exchange 2003 I opened Outlook, copied all of the public folders to my mailbox,

2) Changed the the “Default public folder database” setting to point to the “Public Folder Database <big long number if applicable>” on the Exchange Server 2010 server. Under Organzation Configuration->Mailbox, choose the Mailbox database and right-click for properties, choose Client Settings, browse for the database (like this)

3) Moved my mailbox to Exchange Server 2010 and copied all of the public folders from my mailbox to the All Public Folders.

Email Address Policies

Another gotcha I encountered was the conversion of the email address polices failed with this message:

“The recipient policy “Default Policy” with mailbox manager settings cannot be managed by the current version of Exchange Management Console. Please use a management console with the same version as the object. (shortened for brevity)”

The fix for me, as described here, was to uncheck the Mailbox Management Settings for each Recipient Policy on the Exchange 2003 server. After that the Set-EmailAddressPolicy command worked just fine.

Email Aliases and Security

Several of the mailboxes I had to move had spaces (or other illegal characters) in the Exchange Alias property. For example, this is not acceptable: John Pepper, instead it should just be JohnPepper.

Also, several mailboxes did not have “Include inheritable permissions from this object’s parent” checked. This resulted in several mailbox moves failing with “insufficient rights”.

UPDATE! (5/10/2010)

Distribution Groups and Outlook 2003

I heard today that several people were unable to send emails using the distribution groups, a quick check revealed that the Expansion Server for the groups was still set to the Exchange 2003 server.
To modify the setting open the properties of the distribution group, click Advanced tab, make sure the “Set expansion server” is checked and browse for and select the correct server.

Another gotcha / suprise was the change in communication protocols between Exchange Server 2010 and Outlook 2003. Apparantly Exchange Server 2010 no longer supports UDP, it only supports asynchronous notifications and (as a fallback) a polling interval when communicating updates to Outlook clients. Outlook 2003 only supports UDP and polling… you see the disconnect here?
As a fallback Outlook 2003 will use polling to communicate with the Exchange Server – this causes a weird user experience in Outlook 2003 where (for example) you delete a message and it remains in Outlook until the next polling takes place. You can read more here: “Maximum Polling Frequency is non-default” and here “Outlook 2003 (connected to Exchange 2010) gives unknown error when deleting some messages”

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