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Entourage 2008 and SBS 2008

We have a client who is using Entourage on Mac OSX 10.6.3. We have setup the connection to the Exchange server (Hosted on a SBS 2008) box however it just sits there saying not connected. THe user cannot access his mailbox or the public folders. Here is what has been tried so far.

Using https://ipaddress/ for Exchange server address
Using https://ipaddress/owa for Exchange server address
Using https://ipaddress/exchange for Exchange server address
Adding a host entry for remote.domain.com to point to server's public IP and then using the same combination of the above. The certificate on the server is self signed and issued to remote.domain.com.
Disable SSL on the Exchange virtual directory in IIS.

If i open finder i can put the address https://ipaddress/public and i am prompted for login. Put in the correct credentials and the public folders are shown. Anybody have any ideas on how to solve this issue?
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Syed Mutahir Ali
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Using https://ipaddress/ for Exchange server address
Using  https://ipaddress/owa  for Exchange server address
Using https://ipaddress/exchange  for Exchange server address

is that a public ip address or private ?
is this client on the same lan as the exchange box ?
The first thing I would do is get a real SSL certificate from Godaddy or wherever.  For $30/year, it reduces headaches involved with Outlook anwhere and other devices outside of your physical LAN.

Details on that here:
http://sbs.seandaniel.com/2009/02/installing-godaddy-standard-ssl.html

Personally, I'd add that certificate (and also make sure that autodiscover is setup properly though that's not necessary for this).

Then create a new Entourage account with these values on the accounting settings tab:
account id: username
domain: user's domain
password: user's password

Exchange server: https://remote.domain.com/exchange
check the box for this service requires a secure connection (SSL)


You can get by without buying a third party SSL certificate, but I don't ever recommend that anyone does.  Once you get it, you'll wonder why you ever worked without one - especially if you have workers off-site.

in exchange server address, type "remote.domain.com" without https://
 
http://www.itd.umich.edu/itcsdocs/s4359/
As dmessman has suggested to get a proper ssl certificate - that is always good and saves alot of headaches.
if the client is on the same lan, then type the local sbs server name in exchange server field

sometimes, some lan routers have problems with natloopback and public ip or hostname won't be reachable from withtin that lan.