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

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