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Outlook 2010 Won't connect to server from remote location

i just installed a new Win7 PC at a remote location with MS Office 2010. Outlook 2010 won't connect. I have others PC's in the same remote LAN running Outlook 2003 and 2007 with no issues. This remote site is connected to the the home office between a SonicWall and a LinKsys RVO VPN box. There are no issues getting to home office network resources other than the one Outlook 2010 issue. I can ping the mail server no problem and have checked the hosts file. If I establish a pptp vpn tunnel from this PC to the home office then Outllok 2010 connects. If I kill the pptp vpn clinet Outlook 2010 remains connected. If I reboot I need to re-establish the VPN tunnel again. Any one have any ideas on this? The mail server is Exchange 2003 sp2. one thing that seems to be differnt is that in the past version of Outlook, the user name in the email setup resolves to the persons email address. Usually that resolved to their alias.
Avatar of saintfran

Hi Crdixon,

I think the feature you are looking for is Outlook Anywhere.  It lets Outlook 2010 to connect to the Exchange Server via http without the need for a VPN.

Here are two links that explain it:

Avatar of crdixon


I'm familiar with that. However, I don't want to make any changes to the server side, just the Outlook 2010 client to work like 2003 and 2007.
My Outlook does what you want it to do, these are my settings.  Try check them in your Outlook 2010:
Account Settings
Account Settings
Change (E-mail Tab)
More Settings

Automatically detect connection state is selected (General Tab)
Encrypt data between MS Outlook and MS Exchange is selected (Security Tab)
Negotiate Authentication is selected (Security Tab)

Connect to MS Exchange using HTTP is selected (Connection Tab)

Exchange Proxy Settings
provide the https:// address for the server i.e.
Only connect to proxy servers that have this principal name in their certificate is selected is entered in field
Basic Authentication is selected
Avatar of crdixon


I don't want to use Outlook anywhere. I have a full time VPN tunnel between these offices.
You could also try and manually configure your account using the IP address of the Exchange server instead of its hostname.

Also I come across this for a juniper FW.  The senario might apply to your situation.
Avatar of crdixon


Yes i always put in the ip address and also have it in the hosts file. The problem I think it that it keeps converting the mailbox name form just the alias that I normally see to the person emails address. Very odd.
crdixon, I am having a similar situation.  Client has SBS2008 and Outlook 2010.  In the office, everything works fine.  While at home, they start a Cisco QuickVPN connection and then Outlook and it works fine.  They have traveled accross the country, and now Outlook won't connect.  I can ping the server, explorer the network shares but Outlook still will not connect.  It gives a message that the server is unavailable.  Like you, I don't want to use the HTTP connection option.  Have you had any luck with a resolution?
Avatar of crdixon


No i never got this to work, I ended up downgrading this person's Outlook back to 2003 and everything is working fine with that version. Aside from the connectivity issue, she didn't like Outlook 2010 at all. However, as we move forward we will need to have other people use Outlook 2010 so I'm afraid I'll see this issue again.
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Avatar of crdixon


ok i will try this.
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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.