I am running the community release of ZCS on a CentOS 5x machine. My gateway server is an Astaro Security Gateway which routes the mail internally to the Zimbra server. I have not had any problems until I tries to start using a spam/av service (http://safeguardmail.com/).

Mail is getting processed through safeguard just fine, and is then successfully relayed to my Astaro Gateway (SMTP) server, and it is then sent to the Zimbra server (penguin.johnnystork.ca) but eventually gets bounced? Below is the bounce message when the mail was sent from my Gmail account. The message claims Too Many Hops? Which I cant understand since I still have the same number of servers relaying messages as before? First mail went to Hostgator ---> Astaro Gateway ---> Zimbra. Now the mail is going through SafeGuard --> Astaro Gateway ---> Zimbra, but gets bounced by Zimbra?

I also have all the other logs if needed, but I cant find anything which indicates the problem in Zimbra. I also tried to add the safeguardmail server in the "Inbound SMTP host name" setting, but this did not make any difference?

I am at a loss to figure out why the mail is bouncing/failing simply by routing it through safeguard first.

Anyone have any ideas?


###Bounced message response in Gmail:

The original message was received at Tue, 3 Jan 2012 00:09:11 -0600
from localhost.localdomain [127.0.0.1]

----- The following addresses had permanent fatal errors -----
<stork@openenterprise.ca>
(reason: 554 5.4.6 Too many hops)

----- Transcript of session follows -----
554 5.4.6 Too many hops 29 (25 max): from <johnny.stork@gmail.com> via localhost.localdomain, to <stork@openenterprise.ca>

Final-Recipient: RFC822; stork@openenterprise.ca
Action: failed
Status: 5.4.6
Diagnostic-Code: SMTP; 554 5.4.6 Too many hops
Last-Attempt-Date: Tue, 3 Jan 2012 00:09:11 -0600

####This is a /var/log/zimbra.log entry for the failed messages:

Jan 2 22:31:20 penguin postfix/smtpd[10659]: connect from astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:20 penguin postfix/smtpd[10659]: setting up TLS connection from astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:20 penguin postfix/smtpd[10659]: Anonymous TLS connection established from astaro.johnnystork.ca[192.168.1.1]: TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits)
Jan 2 22:31:20 penguin postfix/smtpd[10659]: 2E42B9C0475: client=astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:20 penguin postfix/cleanup[10662]: 2E42B9C0475: message-id=<CACd5gKYQ3OwV65xKMzyuW7LP6gH5nNG5sS3BCShD8F2VB pCS-Q@mail.gmail.com>
Jan 2 22:31:20 penguin postfix/qmgr[6755]: 2E42B9C0475: from=<johnny.stork@gmail.com>, size=5851, nrcpt=1 (queue active)
Jan 2 22:31:20 penguin postfix/smtpd[10659]: disconnect from astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:20 penguin amavis[6519]: (06519-04) ESMTP::10024 /opt/zimbra/data/amavisd/tmp/amavis-20120102T215003-06519: <johnny.stork@gmail.com> -> <stork@openenterprise.ca> SIZE=5851 Received: from penguin.johnnystork.ca ([127.0.0.1]) by localhost (penguin.johnnystork.ca [127.0.0.1]) (amavisd-new, port 10024) with ESMTP for <stork@openenterprise.ca>; Mon, 2 Jan 2012 22:31:20 -0800 (PST)
Jan 2 22:31:20 penguin amavis[6519]: (06519-04) Checking: RuSXLiDjcEof MYNETS [192.168.1.1] <johnny.stork@gmail.com> -> <stork@openenterprise.ca>
Jan 2 22:31:24 penguin postfix/smtpd[10666]: connect from localhost.localdomain[127.0.0.1]
Jan 2 22:31:24 penguin postfix/smtpd[10666]: 7A7B99C0476: client=localhost.localdomain[127.0.0.1]
Jan 2 22:31:24 penguin postfix/cleanup[10662]: 7A7B99C0476: message-id=<CACd5gKYQ3OwV65xKMzyuW7LP6gH5nNG5sS3BCShD8F2VB pCS-Q@mail.gmail.com>
Jan 2 22:31:24 penguin postfix/qmgr[6755]: 7A7B99C0476: from=<johnny.stork@gmail.com>, size=6327, nrcpt=1 (queue active)
Jan 2 22:31:24 penguin postfix/smtpd[10666]: disconnect from localhost.localdomain[127.0.0.1]
Jan 2 22:31:24 penguin amavis[6519]: (06519-04) FWD via SMTP: <johnny.stork@gmail.com> -> <stork@openenterprise.ca>,BODY=7BIT 250 2.0.0 from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as 7A7B99C0476
Jan 2 22:31:24 penguin amavis[6519]: (06519-04) Passed CLEAN, MYNETS LOCAL [192.168.1.1] [74.125.82.47] <johnny.stork@gmail.com> -> <stork@openenterprise.ca>, Message-ID: <CACd5gKYQ3OwV65xKMzyuW7LP6gH5nNG5sS3BCShD8F2VBp CS-Q@mail.gmail.com>, mail_id: RuSXLiDjcEof, Hits: 2.29, size: 5843, queued_as: 7A7B99C0476, 4288 ms
Jan 2 22:31:24 penguin postfix/smtp[10663]: 2E42B9C0475: to=<stork@openenterprise.ca>, relay=127.0.0.1[127.0.0.1]:10024, delay=4.3, delays=0.04/0/0/4.3, dsn=2.0.0, status=sent (250 2.0.0 from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as 7A7B99C0476)
Jan 2 22:31:24 penguin postfix/qmgr[6755]: 2E42B9C0475: removed
Jan 2 22:31:25 penguin postfix/smtp[10667]: 7A7B99C0476: to=<stork@openenterprise.ca>, relay=gateway2.safeguardmail.net[75.126.136.162]:25, delay=1.4, delays=0.01/0/0.7/0.71, dsn=2.0.0, status=sent (250 2.0.0 message o020VP1066454645aS accepted #554 (o020VO106645464500))
Jan 2 22:31:25 penguin postfix/qmgr[6755]: 7A7B99C0476: removed
Jan 2 22:31:39 penguin postfix/smtpd[10659]: connect from astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:39 penguin postfix/smtpd[10659]: setting up TLS connection from astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:39 penguin postfix/smtpd[10659]: Anonymous TLS connection established from astaro.johnnystork.ca[192.168.1.1]: TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits)
Jan 2 22:31:39 penguin postfix/smtpd[10659]: 69D609C0475: client=astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:39 penguin postfix/cleanup[10662]: 69D609C0475: message-id=<CACd5gKYQ3OwV65xKMzyuW7LP6gH5nNG5sS3BCShD8F2VB pCS-Q@mail.gmail.com>
Jan 2 22:31:39 penguin postfix/qmgr[6755]: 69D609C0475: from=<johnny.stork@gmail.com>, size=7688, nrcpt=1 (queue active)
Jan 2 22:31:39 penguin postfix/smtpd[10659]: disconnect from astaro.johnnystork.ca[192.168.1.1]
Jan 2 22:31:39 penguin amavis[6512]: (06512-18) ESMTP::10024 /opt/zimbra/data/amavisd/tmp/amavis-20120102T190004-06512: <johnny.stork@gmail.com> -> <stork@openenterprise.ca> SIZE=7688 Received: from penguin.johnnystork.ca ([127.0.0.1]) by localhost (penguin.johnnystork.ca [127.0.0.1]) (amavisd-new, port 10024) with ESMTP for <stork@openenterprise.ca>; Mon, 2 Jan 2012 22:31:39 -0800 (PST)
Jan 2 22:31:39 penguin amavis[6512]: (06512-18) Checking: hH91yY0sUeqZ MYNETS [192.168.1.1] <johnny.stork@gmail.com> -> <stork@openenterprise.ca>
Jan 2 22:31:40 penguin postfix/smtpd[10666]: connect from localhost.localdomain[127.0.0.1]
Jan 2 22:31:40 penguin postfix/smtpd[10666]: 24E169C0476: client=localhost.localdomain[127.0.0.1]
Jan 2 22:31:40 penguin postfix/cleanup[10662]: 24E169C0476: message-id=<CACd5gKYQ3OwV65xKMzyuW7LP6gH5nNG5sS3BCShD8F2VB pCS-Q@mail.gmail.com>
Jan 2 22:31:40 penguin postfix/qmgr[6755]: 24E169C0476: from=<johnny.stork@gmail.com>, size=8164, nrcpt=1 (queue active)
Jan 2 22:31:40 penguin postfix/smtpd[10666]: disconnect from localhost.localdomain[127.0.0.1]
Jan 2 22:31:40 penguin amavis[6512]: (06512-18) FWD via SMTP: <johnny.stork@gmail.com> -> <stork@openenterprise.ca>,BODY=7BIT 250 2.0.0 from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as 24E169C0476
Jan 2 22:31:40 penguin amavis[6512]: (06512-18) Passed CLEAN, MYNETS LOCAL [192.168.1.1] [74.125.82.47] <johnny.stork@gmail.com> -> <stork@openenterprise.ca>, Message-ID: <CACd5gKYQ3OwV65xKMzyuW7LP6gH5nNG5sS3BCShD8F2VBp CS-Q@mail.gmail.com>, mail_id: hH91yY0sUeqZ, Hits: 2.29, size: 7679, queued_as: 24E169C0476, 714 ms
Jan 2 22:31:40 penguin postfix/smtp[10663]: 69D609C0475: to=<stork@openenterprise.ca>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.73, delays=0.01/0/0/0.71, dsn=2.0.0, status=sent (250 2.0.0 from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as 24E169C0476)
Jan 2 22:31:40 penguin postfix/qmgr[6755]: 69D609C0475: removed
Jan 2 22:31:41 penguin postfix/smtp[10667]: 24E169C0476: to=<stork@openenterprise.ca>, relay=gateway2.safeguardmail.net[75.126.136.162]:25, delay=1, delays=0/0/0.43/0.61, dsn=2.0.0, status=sent (250 2.0.0 message o020Ve1066454676fY accepted #554 (o020Ve106645467600))
Jan 2 22:31:41 penguin postfix/qmgr[6755]: 24E169C0476: removed