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Entourage can not send/receive remotely through VPN

Posted on 2008-06-12
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Last Modified: 2013-11-30
Here's the situation, and it's driving me up the wall....

I have a Windows SBS2003 server running Exchange 2003 that sits internally behind a firewall handling email.  The firewall is a Symantec 301 running a Symantec client (on the Windows clients).  On the several new MacBooks we're using IPSecuritas to successfully connect to the VPN.  How successful?  Well, file sharing is working out fine.

However, once connected to the VPN Entourage refuses to send or receive email.  There are no errors (that i can find) during receive attempts, but if I try to send email I am greeted by "Error -18597".  I've recently installed SAV11 which I understood to ocassionally have problems with OWA and consequently, Entourage, but OWA is working now so I'm stumped.

Thoughts?
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Question by:AlecEriksson
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by:MiniDevo
ID: 21778481
I guess my first question is, why are you using a third party application for VPN services when Internet Connect, has VPN capabilities? I would try testing with the built in VPN for Mac OS X and test from there.
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Accepted Solution

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AlecEriksson earned 0 total points
ID: 22302176
Turns out the solution was to go into IIS and enable OWA access by IPs in a range outside the internal network.  Apparently the VPN client on OSX (IPSecuritas) passes the internet IP of the remote system through the firewall tunnel.  Whereas on the Symantec client it must in some way tag the remote system with an internal (to the VPN) ip which convinces OWA and subsequently Outlook, to allow access.

Yeesh!

Oh and we use a third party VPN client because I've never managed a successful connection between our Symantec firewall and XP or OSX using anything but a third party app.  
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