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Autodiscover not working on external PC

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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endital1097
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go to https://testexchangeconnectivity.com/ and post results for autodiscover
also, are you getting a login failure?
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ASKER

Attached is a PDF of my results. It passes with alot of green.
au.pdf
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
what happens when you enter your credentials DOMAIN\user and password
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ASKER

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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Cliff Galiher
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ASKER

Thank you both very much for your feedback, i really appreciate it.