Exchange CU9 Migration Issues

It seems that with every migration I do I see unique errors, quirks or bugs that I have not seen before. Recently I was working with a customer who was upgrading from Exchange 2007 to 2013. A pretty common scenario now that Exchange 2013 has been out for two years and Exchange 2007 is creeping closer to its EOL.

The Issues

Here are the two issues I encountered this time:

  • Outlook 2013 not connecting – post migration
  • Coexistence, UM URL and Pop-ups

Outlook 2013 not connecting – post migration

First issue for the migrating users was to find that they could no longer connect to mailbox post migration. First time they open Outlook a message about a change has been made, please close the client message appears. The user does this. Then when Outlook is re-opened the user is prompted for credentials, but can never get passed the prompts or open Outlook. Tried a new profile and a new machine. No luck. Did some digging and it appears that Exchange 2013 is caching the information related to the mailbox. Outlook talks to Exchange 2013 and gets a reply that its mailbox is on Exchange 2007. Then Outlook tries to connect and Exchange 2007 tells Outlook that the mailbox has moved. Then Outlook checks with Exchange 2013 and you have a nice loop.

How to verify your Outlook 2013 client has not updated? Just use the Test E-Mail AutoConfiguration feature that is part of Outlook – Control-Right Mouse Click on the Outlook icon in the system tray:


This will bring up the test pop-up:


Clear the checkboxes in the blue rectangle, enter the email address and password for the user, then click Test.

For my client, we noticed that the information from AutoDiscover had not updated:


I had noticed that before this, that changes I had made on 2007 were not updating AutoDiscover in what I would consider a timely manner. I would change a URL and AutoDiscover would not reflect the changes. An IIS reset on 2007 would produce the same result. If I reset IIS on the Exchange 2013 server, however, AutoDiscover would now reflect the changes. I suspected the same thing was true for the mailbox move.

Resetting IIS did resolve the issue. With a bit of research on the forums, it turns out that many people are having issues. The resolution seems to come down to app pool recycling, more specifically these pools should be recycled to help Outlook connect:

Exchange 2013 CAS
* MSExchangeAutodiscoverAppPool
* MSExchangeRpcProxyFrontEndAppPool

Exchange 2013 Mailbox Server
* MSExchangeAutodiscoverAppPool
* MSExchangeRpcProxyAppPool

These app pools can be restarted in the GUI:

Recycle App Pools

Or they can be restarted with PowerShell:


# Import IIS PowerShell Module
Import-Module WebAdministration -ErrorAction SilentlyContinue

# Get Application Pools
$pools = gci iis:\apppools

# Go through loop to process the right pools
foreach ($line in $pools){
    $name = $line.Name
#    if ($name -eq ("MSExchangeRpcProxyAppPool" -or "MSExchangeRpcProxyFrontEndAppPool" -or "MSExchangeAutodiscoverAppPool")) {
    if ($name -eq "MSExchangeRpcProxyAppPool" -or $name -eq "MSExchangeRpcProxyFrontEndAppPool" -or $name -eq "MSExchangeAutodiscoverAppPool") {
        write-host " ";write-host "Restarting the $name App Pool" -foregroundcolor yellow;write-host " "
        Restart-WebAppPool $name
    } else {
        write-host "No need to restart the $name App Pool." -ForegroundColor cyan

Which looks like this:

Recycle App Pools 2

Coexistence, UM URL and Pop-ups

The next issue we came across was a weird one because before proceeding with the coexistence piece, I made sure I had all of the pieces lined up – URLs for all the various services had to be prepared. The old Exchange 2007 had just the CAS, Mailbox and Hub Transport role installed. No Unified Messaging servers were available in the environment.

After configuring the URLs on 2013 and 2007, we testing Outlook autoconfiguration and Outlook connections in general. When we opened Outlook we received pop-ups for the servers old URLs. I double-checked my work and on the Exchange 2007 server these URLs were correct – OWA, OAB, ActiveSync (EAS) and WebServices (EWS). All the URLs were correct.

We then pulled up the Email AutoConfiguration option for Outlook 2013. We ran the test tool to see what AutoDiscover was supplying to Outlook. The AutoDiscover protocol showed that apparently a Unified Messaging URL had been configured on Exchange 2007. I logged into Exchange 2007 and ran:

get-UMvirtualdirectory -server ex2007 |ft *lurl*

This revealed that the UM was configured with the old domain information:


I simply removed the value by setting the URL to $null (or empty):

get-UMvirtualdirectory -server ex2007 | set-umvirtualdirectory -internalurl $null

After resetting IIS on 2007 and 2013 we were able to verify that AutoDiscover was correct:


Unconfirmed that the cache within Exchange for the mailbox move is a couple of hours. Fixes include IISReset, Recycling the app pools listed above or rebooting the Exchange 2013 server completely.

Other possible solutions: – however this release was generated in Feb of 2014 –> EHLO note on it

Further Reading

Technet article covering settings for this particular issue “Mailbox Cache Age Limit” in particular is worth looking at.


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