Exchange Server 2010 RTM Upgrade and Installation - Phase 2

Thursday, October 22, 2009
These are my notes for phase 2 of my migration from Exchange 2007 SP2 to Exchange 2010 RTM. My notes for phase 1, where I introduced the first Exchange 2010 Hub/CAS/Mailbox server into my existing Exchange 2007 environment, can be read here.

Now in phase 2, I needed to configure the new 2010 server, test mailflow, move the mailboxes, and configure ActiveSync.

I decided to create a third phase, where I will decommission the Exchange 2007 Hub/CAS/Mailbox server, migrate the Windows Server 2008 SP2 Hyper-V host server to Windows Server 2008 R2, and install the Exchange 2010 Edge Transport role on it.

I configured the logging for each server and resubscribed my Edge Transport server. If you don't do this, you'll get the following warning in the Application event log of the 2010 Hub Transport server:
Log Name: Application

Source: MSExchange EdgeSync
Date: 10/22/2009 3:07:25 PM
Event ID: 1032
Task Category: Topology
Level: Warning
Keywords: Classic
User: N/A

Microsoft Exchange EdgeSync can't find the replication credential on to synchronize with Edge server This may happen if joined the current Active Directory site after subscription for was established. To have this Hub Transport server participate in EdgeSync, re-subscribe to the current Active Directory site.
There's no need to remove the old subscription. Just create a new subscription file using the New-EdgeSubscription cmdlet on the Edge Transport server and import it using the New Edge Subscription action in EMC on the 2010 Hub Transport server, as usual. It will update the existing Edge subscription for the new 2010 server.

Next, I reconfigured port forwarding for my Client SMTP Send Connector (TCP port 587) to be directed to the new 2010 server. I tested this using my iPhone, which is connected to my home email using IMAP4 and SMTP. In this configuration, the iPhone gets email from the Exchange 2007 server, but sends email through the Exchange 2010 server. Both incoming and outgoing emails tested fine.

Now I needed to move the mailboxes to the new 2010 server. This is accomplished using the Exchange 2010 Management Console to perform Local Move Requests to the database on the 2010 server. Once the move is completed, I cleared the Move Request in the console to complete the move.

Now it was time to move IMAP services to the new 2010 server. As in previous versions of Exchange, the Microsoft Exchange IMAP4 and Microsoft Exchange POP3 services are set to manual and stopped, by default. I changed the Microsoft Exchange IMAP4 service to automatic and started it. Then I reconfigured port forwarding for IMAP4 (TCP port 143) and IMAP4/TLS (TCP port 993) to be directed to the new server. I sync'd the iPhone using secure IMAP and it worked fine.

Note: I use self-signed certificates for Exchange 2007 and 2010. The iPhone will give a warning saying that the certificate may not be trusted. When you continue anyway, the certificate is automatically installed on the iPhone and you won't be prompted again. Cool!
Next, I used the Microsoft Exchange ActiveSync Connectivity Tests in the Microsoft Exchange Remote Connectivity Analyzer to test that ActiveSync is working properly. This tool allows you to remotely test several aspects of you Exchange infrastructure, including Outlook and ActiveSync AutoDiscover records, ActiveSync functionality, Outlook Anywhere, inbound / outbound SMTP email, and more from a Microsoft-hosted website. Very. Very. Cool. The Exchange team just recently updated the ExRCA to work with Exchange 2010.

Here, I ran into an unexpected problem. The ActiveSync tests were failing in ExRCA with the error, "Exchange ActiveSync returned an HTTP 500 response", as shown below.

Unfortunately, the "Tell me more about this issue and how to resolve it" link refers to a less than helpful article for Exchange 2003. I checked the event logs and found the following error in the Application event log:
Log Name: Application

Source: MSExchange ActiveSync
Date: 10/22/2009 9:18:03 PM
Event ID: 1053
Task Category: Configuration
Level: Error
Keywords: Classic
User: N/A

Exchange ActiveSync doesn't have sufficient permissions to create the "CN=Keith Johnson,CN=Users,DC=expta,DC=com" container under Active Directory user "Active Directory operation failed on This error is not retriable. Additional information: Access is denied.

Active directory response: 00000005: SecErr: DSID-031521D0, problem 4003 (INSUFF_ACCESS_RIGHTS), data 0
Make sure the user has inherited permission granted to domain\Exchange Servers to allow List, Create child, Delete child of object type "msExchangeActiveSyncDevices" and doesn't have any deny permissions that block such operations.
After a bit of research, I discovered that this happens when a user is a member of a Windows built-in group. In my case, the user was a member of Domain Admins. As you probably know, it's best practice to only use admin accounts for administrative functions and to not use them for regular user functions, such as ActiveSync.

To fix the problem, you must remove the user from the built-in group and reconfigure the user's security to apply inheritance (in ADUC, select the Security tab, Advanced, and check Include inheritable permissions from this object's parent). If you don't remove the user from the built-in group, Windows will deselect inheritance.

Once I did all this and retested the ActiveSync functionality using ExRCA, I was ready to configure ActiveSync for my most important user - my wife with her iPhone. It worked like a charm.

There's just a little bit of cleanup to do now. I need to move the Offline Address Book to the new 2010 server and then I can move on to phase 3, where I will decommission the Exchange 2007 server and upgrade the Hyper-V host and Edge Transport server.


  1. This was exactly the information I was looking for. I have just figured out, that you don't have to remove the user from groups like "Domain admins".

    The only setting needed, are the inheritable permissions.

    Btw: I would include the error message you get on the Windows Mobile device. It's 0x86000C0A. You cannot find any information about this error code by using google search.

  2. Thank you so much for this, I was starting to pull my hear out.

    Also, an added thanks to Anonymous for including the ActiveSync error code, and Google for indexing it. :)

  3. Good stuff. Although I did note that ADS turned the inheritance off but the ActiveSync still worked for the affected users.

  4. Ah absolute gem of a post, I'd been pulling my hair out half the night trying to fix the problem, but the inheritances did it!

    Might be worthwhile for novice users to note that in ADUC you have to turn on advanced features on the View menu for the security settings to become available!

  5. yes this one is an absolute gem post ... playing around with that stuff for about 4 hours *omg*

    on my pda the active sync app didn't show that error so i was fucked there too thanks to the windows mobile device center to find the error code!

  6. Thanks for the information. I was able to solve my problem with this.

  7. Hi Jeff, good article, but im looking for phase 1 and can not find it, where can i find it?



  8. Hi Leonardo, I fixed the link at the top of the article. The link is

  9. Thanks Jeff. This problem was really starting to bug me and your post sorted the problem straight away.

  10. Jeff, I too thank you for the post! As seems to be the common theme, I was pulling my hair out for about 4 hours before finding your posting.

    You solved my problem!

  11. you are my savior, i have been looking for this piece of information for a month, thanks a lot.


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