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Autodiscover not working on external PC

Posted on 2010-09-11
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Last Modified: 2012-06-27
Greetings

I'm in the process of setting up an SBS Server 2008 for my company.

I am having an issue with autodiscover on EXTERNAL pc's.

Exchange seems to work fine on computers in the office. If i try and connect my outlook at home to it, i'm asked for login credentials. Check my screenshot.

I have purchased a UCC Cert through GoDaddy and configured it with the following addresses:

autodiscover.vcsli.com
owa.vcsli.com
remote.vcsli.com
VSBS08.vcsli.local (FQDN)
VSBS08 (Server name)

I have created the appropriate A records all pointing to my servers IP

remote.vcsli.com > Server IP
autodiscover.vcsli.com > Server IP
owa.vcsli.com ? Server IP

If you notice in the screenshot, It's try to connect to the local servers FQDN. It also is tryong to connect to the autodiscover URL? OSXP is the home computers name, aialacci is my username.

Screen-shot-2010-09-11-at-4.35.1.jpg
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Question by:VCSLI
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9 Comments
 
LVL 32

Expert Comment

by:endital1097
ID: 33654573
go to https://testexchangeconnectivity.com/ and post results for autodiscover
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LVL 32

Expert Comment

by:endital1097
ID: 33654574
also, are you getting a login failure?
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Author Comment

by:VCSLI
ID: 33654590
Attached is a PDF of my results. It passes with alot of green.
au.pdf
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Best Practices: Disaster Recovery Testing

Besides backup, any IT division should have a disaster recovery plan. You will find a few tips below relating to the development of such a plan and to what issues one should pay special attention in the course of backup planning.

 
LVL 32

Expert Comment

by:endital1097
ID: 33654594
outlook attempted to connect to https://autodiscover.domain.com/autodiscover/autodiscover.xml
since you have an A record for this fqdn and the cert includes this name it was successful
at that point the server will prompt for credentials to obtain your mailbox information
the name you see at this point is dependent on your configuration
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LVL 32

Expert Comment

by:endital1097
ID: 33654599
what happens when you enter your credentials DOMAIN\user and password
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Author Comment

by:VCSLI
ID: 33654615
It tells me that it can not add the account while outlook is open.

I closed outlook, went to Mail in the control panel.

Filled in the info, it asks me for credentials and accepts them. Says it added the Exchange Account.

I open Outlook and am immediately asked for login credentials.

I entered them and it connects to Exchange.

Is it supposed to continually ask for credentials like this? It seems to happen every time Outlook is started. If this is correct behavior, can you explain why? I'm curious.
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LVL 57

Accepted Solution

by:
Cliff Galiher earned 250 total points
ID: 33654712
This is normal default behavior for a machine that is not joined to the domain...which I assume your home PC is not. The idea behind this behavior is that a domain machine already required a domain logon to get into the OS. Single-sign-on rules kick in at this point and multiple authentications should not be necessary as you've already proven you are trusted.
A remote machine that is not on the domain has not done such an authentication. Thus there is no place for single-sign-on and the connection is assumed to be untrusted...thus the prompt for credentials.
-Cliff
 
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LVL 32

Assisted Solution

by:endital1097
endital1097 earned 250 total points
ID: 33654834
yes, externally it will ask for credentials
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Author Closing Comment

by:VCSLI
ID: 33654851
Thank you both very much for your feedback, i really appreciate it.
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