On Jun 6, 2010, at 1:15 AM, Mark Edwards wrote:

> On Jun 5, 2010, at 4:12 PM, Mark Edwards wrote:
> 
>> I rebuilt our ASSP setup (done by someone who is long gone), upgrading it 
>> from 1.2.6 running on Windows Server to 2.0.1 running on Ubuntu 10.4 LTS.
>> 
>> The ASSP sits in front of an Exchange 2007 server connecting through 
>> SMTPListenPort to SMTP Destination, and it relays outgoing mail from 
>> Exchange's send connector via Relay Port on a separate IP to Postfix running 
>> as Relay Host on port 125.
>> 
>> This is a similar to the previous setup, and as far as I can tell its the 
>> standard way to do this.
>> 
>> The old server would log both incoming mail as well as outgoing relayed mail 
>> to logs/maillog.txt, whereas the new one only logs incoming.  Outgoing mail 
>> is clearly passing through the ASSP, as headers are being added and there's 
>> no other way for it to hit postfix.  Is it normal for relay connections to 
>> not get logged?
>> 
>> In addition, I was under the impression that recipients in outgoing relayed 
>> mail would be added to the whitelist.  I have the Exchange server listed in 
>> Accept All Mail, as well as in Allow Relay Connections From.  It appears 
>> that only successful senders are added to the whitelist, however.  Is this 
>> the normal behavior?
>> 
>> I'm wondering if outgoing relayed mail is somehow not being processed at all.
>> 
>> Thanks.
> 
> 
> I made an interesting discovery.  If I conduct a telnet session to the 
> relayport of the ASSP from the Exchange server, the mail is logged in the 
> ASSP maillog.txt.  So, it would seem to be something about how Exchange is 
> sending via its Send Connector that is preventing the mail from being 
> processed by the ASSP.
> 
> However, when I watch both an Exchange connection and a hand-made telnet 
> connection in the SMTP Connections viewer of the ASSP web interface, they 
> appear identical.  Both are coming from the same address (10.10.11.5), and 
> all the other fields are the same.
> 
> Why would one be logged and processed and the other not?

I sorted it out.  Exchange and Postfix were negotiating a TLS connection, which 
was cutting ASSP out of the loop.  Its cool that ASSP happily continued 
transmitting the dialogue, as at least users' mail was being sent successfully.

Setting smtpd_use_tls=no in /etc/postfix/main.cf cleared up the problem, and 
now outgoing mail is logged and contributes to the whitelist.

I'm curious if this is a potential problem with incoming mail on the 
listenPort?  Will ASSP not allow a TLS negotiation on that port, and will this 
cut ASSP out of the conversation?
 
--
Mark Edwards
Audiovisual Coordinator & IT Assistant
Contemporary Jewish Museum
736 Mission Street
San Francisco, CA  94103
 
direct line: 415.655.7802
fax: 415.655.7815


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