Mixed Exchange Environmet

Posted on 2014-03-26
Last Modified: 2016-11-23

I am working on a mail server migration from Exchange 2010 to Exchange 2013. I have about 40 users on Exchange 2010 and so far only 2 accounts on Exchange 2013 (myself and my help desk account). Most of my users was running Outlook 2007, about 5 running Outlook 2010 and one running Outlook 2013.

I am running MS Outlook 2010 and every time close my Outlook and reopen it says in the bottom right hand corner "Connected to Microsoft Exchange" then disconnects and a login pop up box comes up. If I click "Cancel" the message obviously goes away however now in the bottom right hand corner says "Needs Password" and I can't send/receive e-mail.

Tech Specs:
-My laptop is part of domain and I am logged in as a domain user connecting to the exchange server locally on the same network (no site to site or anything)
-I checked my authentication and it is set to NTLM Authentication
-My Server is a Dell R520 running W2K8 R2 Enterprise (not running SBS)

Thoughts? Ideas?
Question by:JustinBMak
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Expert Comment

ID: 39958539
If server belongs to exchange 2010 then use SMTP address as exchange 2010 and if user belongs to exchange 2013 then use SMTP address as exchange 2013.

Author Comment

ID: 39959608
Looking at all of the settings, everything looks good.

Still however, I am confused on your comment.
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 39961148
Run an Autodiscover test in Outlook and confirm the correct information is coming back.
Have you tried to recreate the Outlook profile?

If you create a new user on Exchange 2013, does that work correctly?

What about Outlook Anywhere? Have you used a new host name for Outlook Anywhere on Exchange 2013? Using a trusted SSL certificate?

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Author Comment

ID: 39961505
Hey Simon:

Thanks for replying. So I used the Microsoft Remote Connectivity tool to test my Exchange connection (from the outside).

I tested Outlook anywhere & Outlook over RPC and it all passed. There were a few minor warnings about the SSL Cert, which I don't understand why because I installed my SSL cert from Comodo just fine and made sure I added all of the possible names like: ( ( (

But everything connected with my test account (
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 39961850
What were the warnings? Some of them can just be about trust, which can be ignored. Otherwise not so much.

However it wasn't an external test I was referring to, but an Outlook Autodiscover test.


Author Comment

ID: 39962002
Ah okay.

So I did the test, want me to post the results? From a check, everything looks good here.

Author Comment

ID: 39962011
I even checked Autodiscover settings from Exchange 2013 (see attached)


Author Comment

ID: 39962020
My Certificate is good


Author Comment

ID: 39962024
Oh and one more thing, yes I did recreate my profile actually yesterday.

When I was trying to send mail out as (my support account) that I migrated from Exchange 2010 to 2013 I couldn't I kept getting an error.

When I searched around people said that you need to recreate your profile - so I did and it resolved the issue.
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 39967157
Did you change any of the settings on the Autodiscover virtual directory? If you did then you shouldn't have done - the default settings are usually fine.

Where does Autodiscover point? If you look at the Outlook results, are they coming from the old or the new server? Does it change? You could be having an Autodiscover war, where the old and the new servers are fighting over which host name is published to the domain.


Author Comment

ID: 39967246
Did I change any of the settings on the Autodiscover virtual directory? No

Where does Autodiscover point? It is pointing to my new Exchange Server. I know then because I hold down the Ctrl Key + Right click on my Outlook and check "Test E-Mail Auto Configuration" and when I enter in my account info (and password) all the data the is returned is for the new mail server

Outlook results, new or old? They are all new

The names are different. One is called, and the new one is called Both internal server names are different as well.

Accepted Solution

JustinBMak earned 0 total points
ID: 39970489
Okay. So I gave up and called Microsoft and paid their fee to get the answer.

After 5 minutes into the call I figured it out as soon as he did (the tech).

So, I will help everyone that reads this include the one's that tried to help.

The issue was I had multiple mailboxes on my Microsoft Outlook (,,, and, etc.)

2 Out of the 4 Mailboxes were on Exchange 2013, so two of them were still on Exchange 2010. When you open up your MS Outlook, it is trying to connect to those two Exchange 2010 mailboxes through Outlook Anywhere (basically an outside connection) and because Exchange 2010 was set up for Basic Authentication - it was prompting.

Per Microsoft, you can change Outlook Anywhere by open of EMC and go to:

Server Configuration --> Client Access.

1.) Up at the top has your server name, double click on it and a window will open. At the top it will say "General", "System Settings" and "Outlook Anywhere".

2.) Single left click on "Outlook Anywhere". A few inches down it will say "External Host name:" and have what you have listed for Outlook Anywhere (ex:

3.) Right below that there are two radio dots, one for "Basic Authentication" and another called "NTLM Authentication". Choose the radio dot for NTLM Authentication.

4.) Click on OK.

5.) Open up a command prompt (run it as administrator if you're using user account) and type in iisreset. This will restart two web services:
     IIS Admin Service
     World Wide Web Publishing Service

Once those have finished restarting, open back up Outlook and it should be resolved. If not, wait about 5 minutes (or so) and try again.

Send me a PM (message) if you have any questions or need additional assistance.

Author Closing Comment

ID: 39981025
I have already posted the answer to fix my problem.

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