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Outlook 2010 cannot conect to exchange2010 server throught IPSEC VPN

Posted on 2011-09-20
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Last Modified: 2013-02-15
Outlook 2010 client cannot conect to exchange2010 server throught IPSEC VPN.

Server : Windows Server 2008R2 / Exchange 2010 64 bits
Client  : Windows 7 64b / Outlook 2010 64b
VPN Server : IPSEC VPN
VPN Client : The Grenbow IPSEC Client 5.0

I can conect to the server. I can ping the server on IP and NAME.
I can ad a new exchange account to Outlook (in VPN mode).
I have teste with the admin account.
I can't conect to the user mailbox.
Connect throught HTTP is out. (conection settings)
I can do pretty much everything throught the VPN behalve the Outlook conection.
HELP!
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Question by:cemag
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Expert Comment

by:e_aravind
ID: 36571742
are you planning for the "Outlook rpc-https" or just "Outlook MAPI" connections?

From your description,
- Administrator Outlook profile is working fine
- Normal Outlook users profile is not working?
(what is the error message we are receiving?)
What is the details (screen-shot) @ the OUtlook connection-status window (Outlook @ system-tray; control-key and right=click)
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Author Comment

by:cemag
ID: 36572120
The user is working with is laptop onsite as a domain systeem/user and conect to exchange through the LAN.
On the road of at home is conecting to the company network through IPSEC VPN.
The VPN server is a ZyWall (Hardware)  en the VPN client "TheGrenbowVPN v5.0(soft).
Everything is working perfekt behalve Outlook wich cannot conect to the server.
To test the conection I have tryied to add an Outlook mailbox to the systeem in VPN mode.
It was working when I have used the IP adres of the server in state of the NAME.
When I try to change the user account and conect to the server i get a big NO.
"Cannot establish a conection with the Exchange server..."
The idea is that after establishing a VPN connection the user can open outlook and use it pretty much as he does at his desk. I am not sure that rpc-https can be used through VPN so I ques that MAPI is used. Sure we can use Webmail but the customer demands the full Outlook functionality.
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Author Comment

by:cemag
ID: 36912074
Hello! Anyone? I cannot be the only one...
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Accepted Solution

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e_aravind earned 500 total points
ID: 36923550
IMO, if the end-customer is expecting an full Outlook usage from the remote location...we can just concentrate @ the configuration\testing of the "Outlook Anywhere"

>> The URL to configure the same @ E2010
Enable Outlook Anywhere
http://technet.microsoft.com/en-us/library/bb123542.aspx
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LVL 26

Expert Comment

by:e_aravind
ID: 36923575
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Author Comment

by:cemag
ID: 36923914
This is not what I had in mind bu I wil give it a try... let you guys now...
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Expert Comment

by:e_aravind
ID: 36924442
The advantage of configuring\using the "Outlook Anywhere" is
- we just need the port 443 enabled\opened at firewall and no need to worry about the other ports configurations @ the fireall or any other devices

> On contrast if we have the VPN..then we should be having a overhead of configuring the MAPI access across the devices.
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