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My clients are running Windows 7 x64 and Outlook 2010. My servers are running Windows Server 2012 R2 in addition to Exchange Server 2013 CU15.

I had some major problems with my Exchange 2013 installation, such as Service Error 503 in the ECP and various other errors in the Event Viewer, so I decided to reinstall Exchange. I already did this in a test environment and I replicated the same procedure in my production environment today but there is a problem.

My procedure was as follows:

  1. Create a new VM running Windows Server 2012 R2 + Exchange Server 2013 CU15
  2. Migrate mailboxes from old to new server using the ECP > Migration method
  3. Uninstall Exchange 2013 from the old server
  4. Shutdown the old server and remove from the AD including all DNS entries
  5. Delete client Outlook profile, recreate and restart Outlook

Outlook has downloaded the mailbox fine and I can send/receive emails using Outlook and via my iPhone without an issue.

However when I first open Outlook, it says "trying to connect" for what seems like a good minute or so. Using CTRL and right-clicking the Outlook tray icon, followed by Connection Status, it lists all the connections; there are 4 connections (1x Directory and 3x Mail), except one of the Mail connections has a different server name to the other two. Despite this, it says all connections have been established, but I wondering whether this other server name is the old server and could this be causing the delay to connect each time?

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    Is the SCP and AutoDiscovery entry OK? – BastianW Jan 2 '17 at 12:49
  • Did you have public folders on the old server? If so, did you remove them correctly? Did Exchange 2013 on the old server remove correctly? As a fudge, NETBIOS and DNS Alias can work to get the traffic to point to the new server. – Sembee Jan 2 '17 at 16:13
  • When I test the AutoDiscover, it returns only one hash@domain under the RPC connection, even though there are clearly two different hash@domain server names in connection status. This is the case after removing and recreating the local Outlook profile. There were no public folders on the old server and yes the old Exchange installation was removed without error and prompted a reboot at the end. Since then, the old server has been deleted from the AD and shutdown. Just to note, the internal and external URLs are the same (i.e. mail.domain.com), which internally resolves to the local IP. – Reado Jan 2 '17 at 20:09
  • What does the "different server name" say if it's not pointing to the new server? There could be a staled DNS pointing to the old server. Maybe you can try to update the "host" file on that workstation to point the "different server" to the new server's IP and see if that helps. If it does, it could be a DNS/networking related issue – Lex Jan 3 '17 at 22:27
  • There is a bug in 2013 when migrating users from 2010 to 2013 that you could be seeing here. This may not matter for your situation, but it is simple to try. I found that on about 1/3 of the migrations I did the client autodiscover would not receive the correct updated response from the server for about 24 hours. Restart the MSExchangeAutodiscoverAppPool in IIS and see if that makes any difference. – JBaldridge Jan 5 '17 at 15:21
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Since you saw different server names in Connection Status, there might be another mailbox or account.
Run the command as follows to get that mailbox information. Check the relationship between these two mailboxes/accounts.

Get-Mailbox | where{$_.ExchangeGuid -like"xxxx*"}

Note: the xxxx here is the xxxxxxxxxxxxxxx@domain.com under server name connections in Connection Status.

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