Outlook 2011 for Mac - Exchange Server address changes from public front-end to internal hub server

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sdbyrd

I'm having an issue with our Outlook 2011 Mac clients where you enter the Exchange Server address as https://webmail.company.com while you're connected to the internal network. Outlook can read mail with no issues. You can then disconnect from the network, take it home and it will continue to work fine. However, when you bring it back and connect to the internal network, Outlook will automatically update the Exchange Server address to the internal Hub server address. Again, Outlook works fine on the internal network. The problem is when you are out of the office and try to use Outlook. Since it has the internal address instead of the public address, Outlook no longer works out of the office. Is there a way to prevent Outlook from automatically changing the webmail address to the internal hub server?
 
Hi,

You might want to keep make both the internal and external url the same if your having a split-dns this should not be an issue. By doing this the clients always connect to the same url which is the external one.

Regards,

Johan

Exchange-blog: www.johanveldhuis.nl
 
Johan does present a valid option. Using split DNS so that the internal and external URL's are the same would work.

It sounds like autodiscover is not working externally. Can you run the Outlook Autodiscover test on the Exchange Remote Connectivity Analyzer site? The URL is https://testexchangeconnectivity.com/Default.aspx. This will help troubleshoot possible configuration issues with autodiscover.
 
Re: Outlook 2011 for Mac - Exchange Server address changes from public front-e

I know this is a slightly older thread, my appologies for reviving. However, I am seeing almost the same thing.

I have a single on premise Exchange 2007 server which is fully updated. All windows clients work perfectly, both internally and externally. The problem is the Mac clients. I configure them with the public address, they work fine for a day or two, then they revert to the internal mail server address and stop working externally.

I have tried repair installs, removal and reinstalls, flushing the keychain, removing and re-adding the account, etc. However, the problem just continues to re-occur.

It appears that the Mac reads the SRV records, or something, and changes it's settings accordingly. I have already removed all references to the external domain on the internal DNS, so I am NOT using a split DNS. Autodiscover does work for all clients, internal and external.

Any help would be greatly appreciated.
 
Re: Outlook 2011 for Mac - Exchange Server address changes from public front-e

From what I can find, this problem does not a resolution, other than using the same url for internal and external.
 
Re: Outlook 2011 for Mac - Exchange Server address changes from public front-e

I resolved this issue, and just wanted to post the resolution and information here for anyone else that experiences it.

What I found out was that Office for Mac 2011 does not handle auto-discover "correctly". To specify, Microsoft OS based Office installs use auto-discover to determine the correct settings for configuring Outlook. Mac uses it continually. This will cause your settings to be adjusted to internal only settings during use onsite, after the account has already been configured appropriately for internal & external.

To adjust this, follow this procedure:

  1. Open Outlook is running
  2. Launch the AppleScript Editor and run the following script:

tell application "Microsoft Outlook"

set background autodiscover of exchange account "NameOfAccount" to false

end tell

​

Of course, replace "NameOfAccount" with the account name listed in Outlook's account settings page.
 
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