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Exchange Autodiscover prompting multiple times for user/password

Posted on 2009-04-06
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Last Modified: 2012-06-27
Hi there,

I have, I think, a problem with the Autodiscover feature on an Exchange 2007 setup. It works, however it just prompts for a username and password multiple times before it does. Is this how it's supposed to be?

The setup is Exchange 2007 SP1, on Server 2008 with 3 CAS, 2 Edge and 2 Hub servers, along with 3 Mailbox clusters.

I wonder if anyone has come across a similar issue, or is this just a "feature" ?
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Question by:brislane
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Expert Comment

by:Mestha
ID: 24076251
It shouldn't prompt at all if the client is a member of the domain. While Microsoft may do some things that make everyone scratch their head at times, having something prompt over and over again would not be acceptable.

Repeating prompts means either it is connecting to the wrong place or there is another configuration issue somewhere.

Therefore the first thing to do is ensure that autodiscover.example.com resolves correctly (where example.com is your public domain name).

Use the autodiscover test tool (hold down ctrl while right clicking on the Outlook icon in the system tray and choose Test Email Auto Configuration) to ensure that it is pointing to the correct places.

Simon.
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by:brislane
ID: 24076473
The client is not a member of the domain. It's using Outlook Anywhere to connect.

autodiscover is resolving correctly, or else it wouldn't work at all after prompting for the user/pass several times.
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Mestha earned 2000 total points
ID: 24077451
Autodiscover makes a number of attempts to connect to various URLs, which could be the cause of the prompts. For example it connects to example.com/autodiscover/ etc... so if you don't have the root of your domain configured correctly, then you could get authentication prompts.
As I said above, you need to test Autodiscover and see where it is pointing.
You could also try the Autodiscover test from the Microsoft test site:
https://www.testexchangeconnectivity.com/

Simon.
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