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Configure OWA behind 2 firewalls.

Last Modified: 2010-08-05
I'm trying to configure OWA on my domain.

Here's the setup:
Firewalled Modem at the front (Linksys AM200)
-Ports 25 and 443 forwarded to Router
Firewalled Router (Linksys WRVS4400N)
-Ports 25 and 443 forwarded to SBS 2003
SBS 2003

I have to have the devices setup in this order because the domain is in my home and there are non-domain wireless devices that need to use the router to get an internet connection. So moving the SBS server forward isn't an option. But I shouldn't think it needs to be.

My website is hosted with 1and1 and will continue with them. It is "www.mydomain.com". I have created a sub-domain and modified the DNS so that it points to my IP address which is called "vpn.mydomain.com".

I have configured OWA as the only webservice available on the SBS. When I browse to this address I get a gateway timeout error (504).


I am not using ISA Server. I can browse to the site from the LAN. I cannot telnet from an external location to 443 or 25 using my IP address (might be related to my modem setup, I'm not on site to check this at time of writing). When I look in the settings for the "exchange" site in IIS I have SSL configured with 128-bit encryption.

These are some of my thoughts:

-Do I need to setup a host header for "exchange" so that it can detect an incoming request from the https://vpn.mydomain.com/exchange address, or should it get it automatically?
-Do I need to modify the address I am attempting to connect to so that it is https://SBS.vpn.mydomain.com/exchange? I keep seeing pointers to use FQDN on google and wonder if that means I should include the hostname?

Any help, pointers, advice or other tests I should try will be greatly appreciated
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