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Configure Outlook for external Exchange connection

Posted on 2014-04-23
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Last Modified: 2014-05-11
A small office environment (6 users) using Server 2003 SBS. The Exchange failed and it was decided to use a hosted Exchange from Rackspace instead of repairing it. The problem is that we cannot connect any of the domain PCs Outlooks using any of the methods that Rackspace recommended. I guess this may be a DNS issue? Can anyone suggest a solution that will allow me to configure the Outlooks within a domain to connect to the hosted Exchange servers without removing them from the domain?
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Question by:Buckeroo_Banzai
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Expert Comment

by:Alan Hardisty
ID: 40019435
Have you checked the configuration using the Exchange Test site https://testexchangeconnectivity.com to see where the problem lies?

You should use the Outlook Anywhere test (assuming they have at least Exchange 2007 or higher).

That should give you a good idea of where the problem lies.

Report back with the results if you are none the wiser having read the results.

Have you also removed the Exchange mailboxes locally from your SBS server?

Alan
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Author Comment

by:Buckeroo_Banzai
ID: 40020315
Alan - I will test using the tools you have suggested and get back to you.

I did not remove the users mailboxes on the Exchange server but I did shut down all the Exchange services thinking that it should be sufficient to prevent any problems with Outlook connecting to them.
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Expert Comment

by:Alan Hardisty
ID: 40020343
Okay - no problems.  Try the test tools and you can they use Outlook to test (With Outlook Open, hold down the left-hand CTRL key and Right-Click on the Outlook Icon in the System Tray, then select Test Email-Autoconfiguration> Untick the Guessmart options and fill in the email address and password and click Test) to see what it is doing before you do anything drastic on the server (shutting down the Exchange services should stop Outlook complaining quite happily).

Alan
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Author Comment

by:Buckeroo_Banzai
ID: 40021167
Alan - I will not be at the office location where this server is located until tomorrow. Just wanted you to know that there will be a short delay in running those tests.
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Expert Comment

by:Alan Hardisty
ID: 40021329
No problems - appreciate the update.  As and when you are ready, post an update and I'll pop back and see if any further advice / guidance is needed.

Alan
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Expert Comment

by:kevinhsieh
ID: 40021351
You may need to reconfigure your Outlook clients from scratch because they will continue to look towards your old Exchange server for their mailbox. Just create a new profile in Outlook and see if it works then.
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Author Comment

by:Buckeroo_Banzai
ID: 40021366
kevinhshieh - After my original attempt to connect to the Rackspace hosted Exchange server with the existing Outlook client failed I uninstalled the Office 2007 version they were using and installed Office 2010. Initially I got the same connection error. Then I tried configuring the connection in the Outlook Exchange settings where I could input the name of the Exchange server. This produced a slightly different result where it popped up a window asking for login credentials. Unfortunately it didn't accept any of the ones I provided.
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Expert Comment

by:kevinhsieh
ID: 40021371
It would be your credentials with Rackspace.
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Author Comment

by:Buckeroo_Banzai
ID: 40021376
Yep, tried those. Both the user account credentials and the admin credentials. So close yet it would go no further.
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Expert Comment

by:kevinhsieh
ID: 40021389
Have you tried contacting Rackspace?
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Author Comment

by:Buckeroo_Banzai
ID: 40021393
Yes, I contacted them but they suggested only removing the PCs from the domain. They will not or cannot offer any advice on configuring Outlook beyond what is in their setup documents.
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Expert Comment

by:Alan Hardisty
ID: 40021397
Have you run the Outlook Anywhere test on the test site yet?
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Author Comment

by:Buckeroo_Banzai
ID: 40021404
Not yet. Will be at the location tomorrow to run all the suggested tests.
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Expert Comment

by:Alan Hardisty
ID: 40021410
You can run that now using a web browser with the relevant email address and password - no need to wait until you are onsite.
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Author Comment

by:Buckeroo_Banzai
ID: 40037599
Sorry about the delay in my response, I was unable to access this office until yesterday. Updates: I am now confident I have the DNS records properly configured by using CNAME for autodiscover.  I thought that a good way to get around Outlook always looking to the DC for the exchange server would be to enter the exchange server's address and IP in the HOST file on the PC. That way I figure that it would be forced to resolve the correct address but...it didn't work. Same old problem when I configure Outlook: Name cannot be resolved. Connection to Exchange is unavailable. Outlook must be online. I disabled some Exchange features in IIS too but still no joy. Nslookup on the PC I modified the HOST file on shows:
server gdc-01.servername.local address 192.168.1.2      non-authoratative answer:
name autodiscover.emailsrvr.com address 184.106.31.93   Your thoughts?
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Author Comment

by:Buckeroo_Banzai
ID: 40038749
Update: After further testing I have discovered this. I can connect to the Rackspace Exchange server with Outlook on any computer that is not part of a domain. Any computer that is part of a domain, even if it is not connected to it at the time, will not connect to the Rackspace Exchange server. There must be a way to connect a domain computer!
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Accepted Solution

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Buckeroo_Banzai earned 0 total points
ID: 40046085
Managed to connect using unorthodox config in Outlook. Problem solved.
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Author Closing Comment

by:Buckeroo_Banzai
ID: 40057062
No further ideas were presented.
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