Messages not arriving - deep into filtering and delivery

All --
How is the unique message ID for an outbound message created? I'm seeing a differences in the domain label attached to outgoing messages, and I wonder if this is preventing mail from arriving to a particular (and maybe other) users.
One of my users is having trouble receiving mail from a couple of lists. She gets mail from a couple other lists ont he same server, so we're trying to figure out what the problem is. The current prime suspects are outbound filtering on the network where the server is located, or inbound filtering a tthe ISP (above the user's account, since nothing is going into her 'spam' mailbox).
This is a concern, since she is a principal contributor to our announce-only list (so is paying very close attention to mail sent in and mail received), and it may indicate that messages from this server (or specific lists) are being blocked, which would have an effect on other subscribers.
I've been through the mailman logs and the MTA logs, and I can see that we are, indeed sending mail to her address. It is just not arriving. I wonder if the following has anything to do with it.
So, in doing all of this analysis, I came accross something odd. Two Mesages that DID ARRIVE look like this in my /var/log/maillog:
Mar 31 21:01:31 promedmail postfix/cleanup[32767]: 27A9F758035: message-id=<5158a425.6590700a.0879.ffffb894@mx.google.com> Mar 31 21:01:31 promedmail postfix/qmgr[4400]: 27A9F758035: from=<promed-fra-bounces@promedmail.org>, size=14135, nrcpt=311 (queue active) ... Mar 31 21:01:32 promedmail postfix/smtp[307]: 27A9F758035: to=<pollackmp@mindspring.com>, relay=tummms.chboston.org[134.174.12.42]:25, delay=1.2, delays=0.73/0.07/0.04/0.37, dsn=2.0.0, status=sent (250 2.0.0 1ayt400cs0-1 Message accepted for delivery)
and
Apr 2 02:29:52 promedmail postfix/cleanup[6635]: 54981758035: message-id=<515A428B.50808@gmail.com> Apr 2 02:29:52 promedmail postfix/qmgr[4400]: 54981758035: from=<promed-eafr-bounces@promedmail.org>, size=8554, nrcpt=480 (queue active) ... Apr 2 02:29:52 promedmail postfix/qmgr[4400]: 54981758035: from=<promed-eafr-bounces@promedmail.org>, size=8554, nrcpt=480 (queue active)
while messages that DID NOT ARRIVE all sort of look like this:
Mar 30 04:00:35 promedmail postfix/cleanup[18138]: ACCE0758034: message-id=<201303300400.r2U402Tx030401@healthmap.chip.org> Mar 30 04:00:35 promedmail postfix/qmgr[4400]: ACCE0758034: from=<promed-daily-update-bounces@promedmail.org>, size=9316, nrcpt=500 (queue active) ... Mar 30 04:00:36 promedmail postfix/smtp[18143]: ACCE0758034: to=<pollackmp@mindspring.com>, relay=tummms.chboston.org[134.174.12.42]:25, conn_use=8, delay=2.1, delays=1.1/0.46/0/0.55, dsn=2.0.0, status=sent (250 2.0.0 1b42w6x590-8 Message accepted for delivery)
OK, if you've gotten this far, you'll see that the message-id ends in either mx.google.com or gmail.com (which are popular and common, and go through) and failing messages end in my specialized domain healthmap.chip.org. Is this the sort of thing that causes a problem with delivery? Are we maybe missing some sort of PTR records in the DNS? That is fixable, but I don't understand why some messages get the 'special' domain and others do not.
Thanks for any help you can offer, Drew Tenenholz

- Drew Tenenholz <dtenenholz@rcn.com>:
Have you tried enabling VERP? So there's one message per recipient.
-- Ralf Hildebrandt Charite Universitätsmedizin Berlin ralf.hildebrandt@charite.de Campus Benjamin Franklin http://www.charite.de Hindenburgdamm 30, 12203 Berlin Geschäftsbereich IT, Abt. Netzwerk fon: +49-30-450.570.155

On 4/2/2013 2:22 PM, Drew Tenenholz wrote:
Aside: If you'd post from your subscribed address, you'd avoid moderation delay and possible rejection of your post.
In list posts, unless the list is anonymous, the Message-ID: is the Message-ID of the incoming message. Mailman's internally generated messages and anonymized posts have a Message-ID of the form
Message-ID: mailman.sssss.ttttt.ppppp.listname@hostname
where sssss is a sequence # ttttt is a time returned by Python's time.time() ppppp is the PID of the generating process
One of my users is having trouble receiving mail from a couple of lists.
[...]
I note that all this mail is routed through tummms.chboston.org. What do the MTA logs on that server show?
Note that the <201303300400.r2U402Tx030401@healthmap.chip.org> message id is not a Mailman generated message id. It was either generated by the process that originated the mail or it was added by healthmap.chip.org because the message passed through that MTA without a Message-ID:.
-- Mark Sapiro <mark@msapiro.net> The highway is for gamblers, San Francisco Bay Area, California better use your sense - B. Dylan

Mark Sapiro writes:
Aside: If you'd post from your subscribed address, you'd avoid moderation delay and possible rejection of your post.
I think Drew already knows this, but since Mark mentions the member filter here, I'd like to remind users that if one has several possible posting addresses, Mailman permits subscribing all of them and setting all but one to no-mail. That allows you to post from any such address without receiving duplicates, and (most important) for open subscription lists users can configure this without admin intervention.

- Drew Tenenholz <dtenenholz@rcn.com>:
Have you tried enabling VERP? So there's one message per recipient.
-- Ralf Hildebrandt Charite Universitätsmedizin Berlin ralf.hildebrandt@charite.de Campus Benjamin Franklin http://www.charite.de Hindenburgdamm 30, 12203 Berlin Geschäftsbereich IT, Abt. Netzwerk fon: +49-30-450.570.155

On 4/2/2013 2:22 PM, Drew Tenenholz wrote:
Aside: If you'd post from your subscribed address, you'd avoid moderation delay and possible rejection of your post.
In list posts, unless the list is anonymous, the Message-ID: is the Message-ID of the incoming message. Mailman's internally generated messages and anonymized posts have a Message-ID of the form
Message-ID: mailman.sssss.ttttt.ppppp.listname@hostname
where sssss is a sequence # ttttt is a time returned by Python's time.time() ppppp is the PID of the generating process
One of my users is having trouble receiving mail from a couple of lists.
[...]
I note that all this mail is routed through tummms.chboston.org. What do the MTA logs on that server show?
Note that the <201303300400.r2U402Tx030401@healthmap.chip.org> message id is not a Mailman generated message id. It was either generated by the process that originated the mail or it was added by healthmap.chip.org because the message passed through that MTA without a Message-ID:.
-- Mark Sapiro <mark@msapiro.net> The highway is for gamblers, San Francisco Bay Area, California better use your sense - B. Dylan

Mark Sapiro writes:
Aside: If you'd post from your subscribed address, you'd avoid moderation delay and possible rejection of your post.
I think Drew already knows this, but since Mark mentions the member filter here, I'd like to remind users that if one has several possible posting addresses, Mailman permits subscribing all of them and setting all but one to no-mail. That allows you to post from any such address without receiving duplicates, and (most important) for open subscription lists users can configure this without admin intervention.
participants (4)
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Drew Tenenholz
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Mark Sapiro
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Ralf Hildebrandt
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Stephen J. Turnbull