Have you done any packet captures - compare your working email clients
with what Microsoft is trying to do with outlook?

On Sun, 2013-03-17 at 20:01 -0500, Gerald Waugh wrote:
> On 03/17/2013 06:43 PM, [email protected] wrote:
> 
> > What about NAT?  Is the mail server on the same network as the
> > client, and DNS resolving to a public ip perhaps?
> > 
> > Client makes initial contact to public ip, server responds from the
> > local network address (different ip),  the client isn't expecting a
> > connection from that address, so there is no TCP connection.
> > 
> > Mark
> > 
> thanks for the response, wan and opt1 are bridged.
> 
> remember that all email clients work except for outlook with firewall
> enabled
> and all email clients work including outlook when firewall is
> disabled.
> 
> I think I will reload the pfSense box. What is the latest pfSense
> version?
> 
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