Exchange 2013 - Outlook users unable to reply (receive Non Delivery Report) to a user whose mailbox has been deleted and re-created
Posted by rbTech Staff, Last modified by rbTech Staff on 04 April 2016 11:08 AM

The Exchange 2013 fun du jour...

Exchange Server 2013, Windows Server 2012r2, VMware hypervisor.  Office (Outlook) 2013 on the workstations.
Customer's Exchange server crashed after repeated power failures/ hard power cycles corrupted the Exchange database (insufficient power protection and preventative maintenance were the main contributing factors to a fairly recent Exchange server eating itself from the inside out).  We performed database recovery and were able to remount the damaged database but there was fairly extensive corruption in 2 mailboxes taht necessitated deleting the mailboxes and rebuilding them.

We pulled a copy of the Outlook .pst and .ost files on the workstations, and then used EMS to disable and re-enable the users mailboxes:

disable-mailbox "User name"
enable-mailbox "User name"

The users were able to re-import their mail, calendar and contacts into the database, but other users were receiving NDRs when they tried to reply to pre-crash emails.  We did some digging, rebuilt the GAL, and in our testing realized that OWA users were able to communicate normally with the affected users, including replies to pre-crash emails.

This meant that the issue was limited to Outlook, and related in some way to the locally cached addresses.  As an experiment, we added the X.500 address in ECP, which didn't do a darned thing so we deleted it again.  But we had a clear direction to look, so we did some more Googling and came across this article:

We pulled the Outlook identifier by opening a previously received message on another user's machine, and opening the contact's "Outlook Properties" tab. We compared that string to the one returned by the following command in the Exchange Management Shell:

Get-Mailbox "User name" | fl LegacyExchangeDN

Viola!! The strings were not the same!
To resolve, we ran adsiedit (holy pucker factor, batman...) and updated the LegacyExchangeDN for the user to the old value, had the sending users restart Outlook for good measure, and they were able to exchange emails normally once again.

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