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Autodiscover not working on external PC


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:

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.

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2 Solutions
go to https://testexchangeconnectivity.com/ and post results for autodiscover
also, are you getting a login failure?
VCSLIAuthor Commented:
Attached is a PDF of my results. It passes with alot of green.
Creating Active Directory Users from a Text File

If your organization has a need to mass-create AD user accounts, watch this video to see how its done without the need for scripting or other unnecessary complexities.

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
VCSLIAuthor Commented:
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.
Cliff GaliherCommented:
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.
yes, externally it will ask for credentials
VCSLIAuthor Commented:
Thank you both very much for your feedback, i really appreciate it.
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