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Access SBS 2008 Exchange 2007 using Outlook without VPN

Posted on 2009-04-12
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Last Modified: 2012-08-13
I recently setup an SBS 2008 box and would like to know the steps to make Outlook 2007 and Outlook 2003 clients able to connect to server without having to use VPN.
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Question by:jeffreychorba
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17 Comments
 
LVL 5

Expert Comment

by:Member_2_4708244
ID: 24127845
What you ar elooking for outlook anywhere:

http://technet.microsoft.com/en-us/library/cc179036.aspx
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LVL 3

Expert Comment

by:rbeckerdite
ID: 24127951
this should do it:
http://office.microsoft.com/en-us/outlook/HP101024441033.aspx

It is called Outlook Anywhere access and you basically publish OWA access to the internet via your firewall and use a special connection configuration in your outlook.
 
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Author Comment

by:jeffreychorba
ID: 24129003
I looked at both of the above posts and it appears I have it setup as shown.  What ports neet to be forwarded for this feature?  I already have 443, 80, 25, 110.

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LVL 5

Expert Comment

by:Member_2_4708244
ID: 24129021
Port 80 only. It used to be called RPC over HTTP in exchange 2003, so it only uses HTTP (port 80), or HTTPS (port 433).
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Expert Comment

by:rbeckerdite
ID: 24129790
can you access OWA?
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Author Comment

by:jeffreychorba
ID: 24129805
Yes
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LVL 3

Expert Comment

by:rbeckerdite
ID: 24129835
And the configuration for outlook does not connect? using RPC over HTTP or Outlook Anywhere access?  Make sure that your client PC outside your firewall can resolve the exchange server name to the external port of the firewall.  To test you could add a Hosts file entry.
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Author Comment

by:jeffreychorba
ID: 24129870
Maybe you can elighten on the config.  In the field that asks for exchange server name would you use the unc name of the exchange server or the url?  I know in the proxy setup you use the url.

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LVL 3

Expert Comment

by:rbeckerdite
ID: 24129909
the link i posted above has pretty specific instructions but it is the internet facing unc pathname from what i read. Check the article out it seams pretty informative.
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LVL 39

Expert Comment

by:Philip Elder
ID: 24129979
Are you using the self-issued SBS SSL certificate? If so, then you need to install the certificate package on all of the remotely connecting Outlooks to get things working.
In SBS 2008, the feature is called Outlook Anywhere and the Help item with specific to your SBS network is found in the Remote Web Workplace.
Philip
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Author Comment

by:jeffreychorba
ID: 24130053
I am not sure if I am?  I know when I connect to the OWA it says there is a problem with the certificate and then it lets me in anyway?  
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LVL 39

Expert Comment

by:Philip Elder
ID: 24130332
You are using the self-issued certificate.
Save yourself a lot of hassle, get yourself an inexpensive third party trusted certificate using the wizard built into SBS and an SSL provider.
Believe me, it is well worth it.
http://sbs.seandaniel.com/2009/02/installing-godaddy-standard-ssl.html
Philip
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LVL 5

Expert Comment

by:Member_2_4708244
ID: 24132834
Or you could just go to OWA, and when the certificate error comes up you can install the certificate and this will resolve that issue, if your PC doesnt trust the certificate outlook will not connect.
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LVL 39

Expert Comment

by:Philip Elder
ID: 24132877
You cannot install the self-issued SBS 2008 as you could the SBS 2003 one.

The SBS 2008 self-issued certificate has to be installed via USB key. The installer zip file is in the default Public share.

Again, you are better off with a third party certificate.

Philip
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Author Comment

by:jeffreychorba
ID: 24181752
I installed the key and it still does not work.
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Author Comment

by:jeffreychorba
ID: 24181755
when it connects to the exchange server (or attempts) I am prompted to enter my username and password.  After I do this it returns to the logon screen again?
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LVL 39

Accepted Solution

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Philip Elder earned 500 total points
ID: 24181890
The proper Outlook logon format:

Domain\UserName
My Crazy P@ssw0rd!

Philip
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