> Have you set debugging on the Mac server?

It was. Problem is that I cannot search the logs for the above e-mail,  
because they have already rolled over, but I did manage to get the  
amavisd log for the e-mail. It's long (despite it being only two  
seconds of conversation), so I won't include it all, here, but it  
seems to be normal, in that the mail seems to have come internally to  
the spam filter. Here's the beginning of the conversation:

Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-10)  
loaded base policy bank
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-10)  
lookup_ip_acl (inet_acl): key="127.0.0.1" matches "127.0.0.1", result=1
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-10)  
process_request: fileno sock=13, STDIN=0, STDOUT=1
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
SMTP> 220 [127.0.0.1] ESMTP amavisd-new service ready
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
SMTP< EHLO mymxserver.com\r\n
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-[127.0.0.1]
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-VRFY
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-PIPELINING
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-SIZE
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-ENHANCEDSTATUSCODES
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-8BITMIME
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250-DSN
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250 XFORWARD NAME ADDR PROTO HELO
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP< XFORWARD NAME=localhost ADDR=127.0.0.1\r\n
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250 2.5.0 Ok XFORWARD
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP< XFORWARD PROTO=ESMTP HELO=mout3.freenet.de\r\n
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250 2.5.0 Ok XFORWARD
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP< MAIL FROM:<[email protected]> SIZE=7630\r\n
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
check_mail_begin_task: task_count=11
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
lookup_ip_acl (mynetworks): key="127.0.0.1" matches "127.0.0.0/8",  
result=1
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
loaded policy bank "MYNETS"
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
lookup (debug_sender) => undef, "[email protected]" does not match
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250 2.1.0 Sender <[email protected]> OK
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP< RCPT TO:<[email protected]> ORCPT=rfc822;[email protected] 
\r\n
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 250 2.1.5 Recipient <[email protected]> OK
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP< DATA\r\n
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP::10024 /var/amavis/tmp/amavis-20090728T133830-26486: <[email protected] 
 > -> <[email protected]> SIZE=7630 Received: from  
mymxserver.com ([127.0.0.1]) by localhost (mymxserver.com [127.0.0.1])  
(amavisd-new, port 10024) with ESMTP for <[email protected]>;  
Tue, 28 Jul 2009 14:32:46 -0400 (EDT)
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP> 354 End data with <CR><LF>.<CR><LF>
Jul 28 14:32:46 mymxserver.com /usr/bin/amavisd[26486]: (26486-11)  
ESMTP< .<CR><LF>
:
:
:

The only event that was even close was two seconds from the assp log:

Jul 28 14:32:48 mini lmtpunix[27938]: Delivered: 
<[email protected] 
 > to mailbox: user.myuser

This was at the time of the end of the amavisd log processing of this  
message, so I imagine this accounts for the two second difference of  
the two log sequences above.

All this seems normal, but I'm not the expert in this. It still does  
not indicate how the mail got to amavisd internally but without being  
processed through assp. The assp log only shows mail from freenet.de  
on 24th. July and 26th. July. :-/

In my research, I did find this:

http://developer.apple.com/documentation/Darwin/Reference/ManPages/man8/lmtp.8.html

Note the bugs section. Not sure if that helps in this case, but it  
does indicate a potential for problems.

FWIW, my firewall is set up to refuse all but allowed TCP traffic in.  
Note that port 24 mentioned in the Apple article is not open to  
outside computers.

I just had a thought. I don't remember the exact times of my restarts  
of the server box during maintenance. Perhaps it's possible that the  
mail managed to get through as the various processes started up? I'm  
not convinced that this would be the only time at which the problem is  
occurring, but I do see this as potential for some mail to skip past  
assp. Mind you, assp is the process that has the ports open to the  
outside, not the mail server, so I'm still confused about possible  
causes of this.

T.

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