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



----- Reply message -----
From: "Gerald Waugh" <[email protected]>
To: "pfSense support and discussion" <[email protected]>
Subject: [pfSense] Microsoft Outlook Blocked
Date: Sun, Mar 17, 2013 7:02 pm
On 03/17/2013 05:36 PM, Chris Buechler 
wrote:



On Sun, Mar 17, 2013 at 4:47 PM, Ermal Lu&ccedil;i <[email protected]> wrote: 



Try enabling on the rule to allow ip options. 
It might be that the packets are being dropped due to having ip options in 
them. 




Outlook shouldn't be using IP options, we'd have had a flood of 
problem reports if that were the case with any degree of consistency. 

Without having a packet capture it's hard to say. My guess based on 
the description is the machine with Outlook has a network 
misconfiguration of sorts where its traffic isn't hitting the firewall 

Thanks for the response.

It is several Outlook IPs that will not work correctly.

the outlook client connects but does not complete and error on 
server is "no auth attempts"

error on the client:

Task '[email protected] - Receiving' reported error 
(0x8004210A) : 'The operation timed out waiting for a response 
from the receiving (POP) server. If you continue to receive this 
message, contact your server administrator or Internet service 
provider (ISP).'
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