Thanks KevinH, I had filed a bug in Zimbra's bugzilla - #9480.
Thanks anand. My thoughts exactly - Postifx will re-write the To: message header when there is no To and is why I'm so confused... HOLD ON...
your comment
Please understand the difference between RCPT TO/MAIL FROM envelope addresses and To:, From:, Cc: message headers.
made me take a look at what I was doing - sending mail via telnet below:telnet mail.domain.tld 25
220 mail.domain.tld ESMTP Postfix
HELO testmachine
250 mail.domain.tld
MAIL FROM:<test@test.com>
250 Ok
RCPT TO:<something@domain.tld>
250 Ok
DATA
354 End data with <CR><LF>.<CR><LF>
Subject: test catchall
testing again
.
250 Ok: queued as 24F425A85B3
quit
221 Bye
I realize now what I've done wrong, first I tested using a MUA like thunderbird and it worked (I should have done this from the start). Then I retested using the correct commands below which also worked.220 mail.domain.tld ESMTP Postfix
HELO testmachine
250 mail.domain.tld
MAIL FROM:<test@test.com>
250 Ok
RCPT TO:<something@domain.tld>
250 Ok
DATA
354 End data with <CR><LF>.<CR><LF>
Date: 11 Aug 2006 11:45:00 From: test@test.com To: something@domain.tld Subject: test catchall testing again .
250 Ok: queued as D06E05A85B3
quit
221 Bye
When seting up a mail server I'll always test some initial things via telnet first. I'll test virus patterns like Eicar-Test-Signature to test the anti-virus daemon, sometimes I'll cheat and not put the full message headers in for this test, not thinking. Thanks again for guiding me down the right path, I'll also post a reply in bugzilla to close the bug.