John, > Oct 5 00:10:22 myhost postfix/smtp[28713]: 125BC2400A7: > to=<fred.blo...@abc.tld>, relay=mail.abc.tld[123.456.789.123]:25, > delay=187500, delays=186888/0.01/0.16/612, dsn=4.4.2, status=deferred > (conversation with mail.abc.tld[123.456.789.123] timed out while sending > end of data -- message may be sent more than once) > > My understanding is that the first message is the original, and the > second and subsequent are postfix retrying the delivery. > my postconf -n output follows below,
Your message probably hit one of several Cisco PIX/ASA bugs related to mail header section parsing: http://www.arschkrebs.de/postfix/postfix_cisco_pix_bugs.shtml > 1) Am I misconfigured? Probably not. > 2) How can I handle this sort of problem in future? If it is your PIX or ASA or you can establish a contact with their hostmaster, the box should be upgraded, or the smtp protocol fixup (mis)feature turned off - best to do both. If it is entirely out of control, removing a DKIM signature header field for mail to such site will probably help. Ralf posted some workaround here some time ago. Mark