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Outlook Anywhere on Outlook 2010

Microsoft Exchange Proxy SettingsAccount SettingHi,
  I am trying to setup Outlook Anywhere in Outlook 2010. I can make it work if I keep VPN session to the network, but the moment I disconnect the VPN connection, then My Outlook fails to open.

  Users can access outlook email on IE by "https://remote.DomainName.com/owa".
  Users also can sync email on smartphones using server name  "remote.DomainName.com".

  How can I set up Outlook Anywhere w/o having to open a VPN connection?
  As seen in the screenshot above, I entered "remote.DomainName.com" thinking that Outlook will try to connect to our Exchange Server via remote.DomainName.com and open the mailbox with Server name and User name.

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3 Solutions
Rob WilliamsCommented:
Check the box "Only connect to proxy servers that have this principal name in their certificate" and in the box enter:
Rob WilliamsCommented:
ps- The following outlines it in detail:

This assumes you have a certificate and public DNS configured but I assume that is the case since the phones can connect.

When the user first connects using Outlook Anywhere they will be prompted for their username and password, authentication is not automatic as it would be with the VPN connected.  When doing so, for the user name use the format  domain\username  such as  abc\tjones
sgleeAuthor Commented:
 You were right. After posting the question, I continued to played with it and got it working finally after installing SBS2011 default certificate on the computer. I fount out that Certificate installation added "msstd:remote.domainname.com" in Exchange Proxy Setting window. That was what's missing before posting my question.

 Since we are on the subject, let me ask you this.

 Initially I had to establish VPN connection to the network when creating Outlook Profile. Without VPN connection, Outlook did not recognize the Exchange Server Name because it simply did not exist outside of the network.

 Is it possible to create Outlook Anywhere from the scratch without the VPN connection from outside of the network?
Rob WilliamsCommented:
Firstly you would be best to buy a 3rd party certificate from GoDaddy or similar.  These certificates are automatically accepted by Windows/Internet Explorer and smart phones, so there is no need to install on the connecting device.  It saves a lot of headaches, especially with smartphones.  To install see:

If you are on the LAN or connected by VPN, running Exchange 2007 or newer, using Outlook 2007 or newer, and have installed a 3rd party certificate, Outlook, including Outlook anywhere, should automatically configure itself.

If you are connecting remotely, are not using a VPN, and have not already configured Outlook Anywhere, you will need to manually configure outlook and Outlook Anywhere it as per instructions in my previous post, but with a 3rd party certificate you do not have to install one.

Usually I join the PC to the domain and just open outlook as the user while on the LAN or connected by VPN during the initial PC/laptop set up, then it is done.
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