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Outlook setup with Exchange 2010

I am having issue setting up an account in Outlook 2007 with a new Exchange 2010 server. When I go to control panel -> Mail to setup the Exchange account, after entering name/email address/password, I could to 1) Establish network connection and 2) Search for test.user@testdomain.com server settings. However, I kept getting the username/password prompt and eventually the error message:

"The action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."

I am able to login and send/receive emails with the account via OWA, which means there's no AD or  password issue here. I could go thru the first 2 steps during the setup which means autodiscover is working fine. So what makes it keep prompting the login box and fail to authenticate?

P.S. I also ran the Outlook Autodiscover option from Remote Connectivity Analyzer on the Exchange 2010 server and the test completed successfully.
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wesdeneo
Asked:
wesdeneo
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1 Solution
 
Dan ArseneauCommented:
If you look at the prompt, does it return a server name?  It may be trying to authenticate against Exchange 2007 Public Folders.
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mrbrain646Commented:
https://www.testexchangeconnectivity.com/
try this and check your ssl certficates
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uescompCommented:
open outlook and have it detect the account automatically vs setting it up via control panel.  If you are prompt for a username/password check to see if there are any saved passwords. To check those open run command and type: control userpasswords2 > click advanced tab > managed passwords, clear the passwords (if any).  Otherwise try typing your domain name in front of the username if prompt.

Example Username:  Domain\uescomp
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wesdeneoAuthor Commented:
@DanArseneau: Yes, it is showing the right server FQDN

@mrbrain646: Yes, that's the site where I ran the Microsoft Office Outlook Connectivity Tests with Outlook Autodiscover option. The SSL certificate was installed just yesterday and is showing valid from the test.
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wesdeneoAuthor Commented:
@uescomp: There is no saved passwords as this is a new AD user created in the test domain. I tried using domain\username then got the aforementioned error message:


"The action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."


If I don't include the domain, it just keeps prompting the login window
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Dan ArseneauCommented:
Tools - Account settings - Change... - More settings... - Connection - Outlook Anywhere checkbox.

Enabled?
Click on the Exchange Proxy Settings... button

Remove "only connect to proxy servers that have this principal name in their certificate".

I had this issue a while back and it helped with Outlook 2007
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wesdeneoAuthor Commented:
@DanArseneau: Just tried. This time it gives me a "Your server or mailbox names cannot be resolved"

Also when I click on "Check Name", I can see the Account Settings window in the background showing the new Exchange Server account (my other accounts in Outlook are POP/SMTP), but for some reason it's just not authenticating (even though OWA works perfectly fine).
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Dan ArseneauCommented:
Change the NTLM authentication to Basic and see if that helps.  It may be set that way on the server.  Not recommended but possible.
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uescompCommented:
either that or check your services and make sure exchange services are running (possible reboot).  I would also double check authentication as DanArseneau pointed out.
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wesdeneoAuthor Commented:
Just checked Outlook Anywhere settings on Exchange server, it was set to NTLM. I set it to basic and use basic on my Outlook end but still no cigar.

for some reason Exchange is able to authenticate via OWA but not Outlook, what gives?
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wesdeneoAuthor Commented:
Also, just for kicks, I tried setting up connection with the same account using either POP or IMAP. In both cases they worked. This should eliminate the possibility with the exchange certificate problem.
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Dan ArseneauCommented:
Start - Run - fixmapi and hit Enter.
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JuusoConnectaCommented:
To verify everything go to exchange management shell and type the following for a user who's name cannot be resolved:

test-outlookwebservices -identity firstname.lastname@domain.com | fl (or ft -autosize) and post your results here.

In outlook when setting up a new profil, instead of using autodiscover choose "Manually set-up". When you come to the field where you enter exchange server name and a username choose more settings and do the following -> Security tab -> make sure to mark "Encrypt data between microsoft office outlook and microsoft Exchange" and "logon network security is set to "Negotiate Authentication".

Under connection -> Outlook Anywhere -> Mark "Connect to microsoft Exchange using HTTP: -> click exchange proxy settings -> in connection settings typ in (after https:) webmail.yourdomain.com (the webmail address that is..) -> mark "Connect using SSL only -> Mark "Only connect to proxy servers that have this principal name in their ceritifcate -> and type : msstd:webmail.yourdomain.com -> set authentication to Basic,

cheers
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wesdeneoAuthor Commented:
I found the solution for my own problem from this blog post:

http://messagexchange.blogspot.com/2008/12/outlook-anywhere-failing-rpc-end-points.html

Basically I receive the exact same RPC error from the second screenshot. Applied the registry fix, reboot and it's good to go.

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Glen KnightCommented:
This question has been classified as abandoned and is being closed as part of the Cleanup Program. See my comment at the end of the question for more details.
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