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Outlook anywhere for Exchange 2010 not working

Posted on 2012-09-04
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Last Modified: 2012-09-04
Hi There,

I'm troubleshooting outlook anywhere feature on a Exchange 2010 SP2.

What I did:

1. Created an A record on external DNS: webmail.domain.com and pointed to firewall

2. Included webmail.domain.com to existing SSL/UCC/SAN - Requested a new certificate from EMC, Re-key from CA and installed in Exchange via EMC

3. Enabled Outlook Anywhere from EMC using host name webmail.domain.com


Outlook 2010 clients (outside the LAN)  receive the following error:

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

Outlook Anywhere:
ticked (connect to MS Exchange via HTTP)

Exchange proxy settings:
Connection Settings

https://webmail.domain.com
(ticked) connect using SSL only

(empty) only connect to proxy servers....

Proxy authentications settings:
(NTLM)


Any suggestions would be appreciated.

Thanks,
Rod
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Question by:Rodrigo Carrilho
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Expert Comment

by:ronnypot
ID: 38362993
You need to change the Proxy authentication settings to basic. This is the default configuration for outlook anywhere.

some information about publishing outlook anywhere with NTLM look here: http://ucoutloud.blogspot.nl/2011/07/outlook-anywhere-ntlm-authentication-by.html
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Author Comment

by:Rodrigo Carrilho
ID: 38363356
thanks for your comment. Am I right to say  I NTLM will give users another layer of security?

I was following the steps from http://exchangeserverpro.com/how-to-configure-exchange-server-2010-outlook-anywhere
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Accepted Solution

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ronnypot earned 2000 total points
ID: 38363383
Both your link as the one I posted give some explaination of the differences between basic  and NTLM authentication.

As written "However NTLM may not work with some firewalls or ISA Server publishing scenarios." it depends on your configuration if NTLM will work. I would suggest first try basic authentication and see if this works fine, if so you can try if you can get NTLM to work.
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