On Wed, 6 Feb 2013 16:54:58 +0000, John Corwin <[log in to unmask]> wrote:

>Received: from pls (192.168.100.23) by mail.pageinc.org (192.168.100.18) with
>Microsoft SMTP Server id 14.1.438.0; Tue, 5 Feb 2013 18:49:55 -0500

 0:08:51 delay here

>Received: by LSERV.PAGEINC.ORG (LISTSERV-TCP/IP release 16.0) with spool id
>          97759 for [log in to unmask]; Tue, 5 Feb 2013
>          18:41:04 -0500
 2:34:01 delay here

>Approved-By: [log in to unmask]

>Received: from mail.pageinc.org (sem0.pageinc.org [192.168.100.18]) by
>          LSERV.PAGEINC.ORG (SMTPL release 1.1a) (envelope-from
>          <[log in to unmask]>) for [log in to unmask]
>          with TCP; Tue, 5 Feb 2013 16:07:03 -0500
  0:01:59 delay here

>Received: from SEM0.pageinc.org ([fe80::7d76:980e:191f:f765]) by
>          sem0.pageinc.org ([fe80::7d76:980e:191f:f765%12]) with mapi id
>          14.01.0438.000; Tue, 5 Feb 2013 16:05:04 -0500

There certainly is a ~2 hour delay in the middle.  You need to consult the
LISTSERV log to see exactly when the message was actually approved.  The 2
hours could simply be a delay in the approval process.  Note that the approval
request email could have been delayed (not shown here) getting to the approver
and then again getting back to LISTSERV (also not shown here).  Note that you
can approve such messages via the LISTSERV WWW Interface with only a few
seconds delay, so you don't need to rely only on the approval email.

If the approval was made shortly after LISTSERV received the message at Tue, 5
Feb 2013 16:07:03 -0500 then the LISTSERV log would show what else LISTSERV
was busy doing for the ~2 hours.  

The other delays are probably normal for your system.  The ~2 min at the
beginning (sender to LISTSERV) is maybe a little long but not abnormal and may
simply be due to a large message size.  The ~9 min delay in receipt of email
back to your mailbox seems normal for the mailer being very busy with the
x,000 emails it has to send out.  Typically these are done in alphabetic order
by domain (A-Z) and P (PAGEINC.ORG) is well past the middle of the alphabet so
a delivery delay is normal for you.

In terms of the other 2 email headers it seems clear that your system clocks
on the various systems are far out of sync.  For example, your email was
delivered 2 min before it was sent:

>My Header
>*****
>Received: from pls (192.168.100.23) by mail.pageinc.org (192.168.100.18) with
>Microsoft SMTP Server id 14.1.438.0; Wed, 6 Feb 2013 10:42:21 -0500

>Received: by LSERV.PAGEINC.ORG (LISTSERV-TCP/IP release 16.0) with spool id
>          103130 for [log in to unmask]; Wed, 6 Feb 2013
>          10:44:25 -0500

This is of course impossible so the clocks must be out of sync.

>My Boss's Header
>*****
>Received: from pls (192.168.100.23) by mail.pageinc.org (192.168.100.18) with
>Microsoft SMTP Server id 14.1.438.0; Wed, 6 Feb 2013 10:58:13 -0500

>Received: by LSERV.PAGEINC.ORG (LISTSERV-TCP/IP release 16.0) with spool id
>          103130 for [log in to unmask]; Wed, 6 Feb 2013
>          10:44:25 -0500

I would take a look at the ~\Inetpub\mailroot\Queue folder for SMTPSVC.  It
may have a lot of mail in it going nowhere.  This could cause delivery delays.

i.e. I think your problems are likely to be in the SMTPSVC mailer, not in
LISTSERV.

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