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Outlook changes proxy settings and keeps prompting for username and password

Posted on 2011-03-13
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Last Modified: 2012-05-11
Our server environment has been SBS2003 with Windows 7 clients. We had an old server so we are using a Hosted Exchange service that we are very happy with. We recently upgraded to SBS2008 and I am moving everyone over to it as we speak. My problem is that when I move the clients to the new server, my proxy settings in Outlook change to connect to the local server even though I set them to connect to our hosted exchange. I change them back and close Outlook and when I reopen Outlook, they are pointed to remote.(mydomain).com again.

Is this a GP or something else? We would like to continue to use our hosted Exchange solution for now.

Thanks.
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Question by:TcAnthony
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Expert Comment

by:viveksahu
ID: 35122088
hi,

Iinto IIS Manager, opened SBS Web Applications, Select Autodiscover, double click SSL settings (you have to scroll down to see it), check Accept instead of ignore or require, and Apply. Also repeat it for owa, remote, Rpc, RpcWithCert (possibly don't have to do all these). Restarted Web Publishing and Joy Joy Joy!!!
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by:TcAnthony
ID: 35122545
Thanks for the reply. Unfortunately, no joy. Still getting the prompting from the local server.
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Expert Comment

by:Cliff Galiher
ID: 35122749
autodiscover is still kicking in and thus resetting Outlook for the local machine. SBS *really* was designed to keep Exchange in-house and running it with hosted Exchange is a ver difficult proposition. You'll have to uninstall Exchange and then work through a series of post-uninstall issues.

Have backups!!!

http://technet.microsoft.com/en-us/library/dd728003(WS.10).aspx
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Author Comment

by:TcAnthony
ID: 35122808
I was really hoping to not have to do something so drastic. SBS can have some MAJOR issues when you start taking things away like that. Can there be any other option?
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Expert Comment

by:Cliff Galiher
ID: 35123790
Sadly you are already down that road by trying to run SBS with hosted Exchange services. Yes, SBS can have complaints when you take stuff away, but you've *already* taken away in-house mail which is why you are having the issues you are having. At least going down this path is completing that process and is putting you in a truly supported (albeit unorthodox) state as that documentation is provided by MS and includes a supported topology. Any workarounds you try to do is actually going to be unsupported from an MS standpoint, so this really is one of the better options.

-Cliff
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Accepted Solution

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TcAnthony earned 0 total points
ID: 35123838
JoyJoy! My Dell Support guy fixed me up in a jiffy. He made a quick change in the Exchange Management Shell.
Set-ClientAccessServer -Identity dc1 -AutoDiscoverServiceInternalUri
https://(hostedexchange.com)/Autodiscover/Autodiscover.xml

Works great!! They have great software support, even on a Sunday afternoon.

Thanks.
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Expert Comment

by:Cliff Galiher
ID: 35123858
Just be aware that the SBS wizards are unaware of that change and unexpected results will now occur regularly when doing maintenance-type work within Exchange using the wizards. That is one of those unsupported scenarios I was referencing.

-Cliff
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Author Comment

by:TcAnthony
ID: 35199365
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Author Closing Comment

by:TcAnthony
ID: 35230058
My own solution
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