Some email addresses won't send - sometimes.

I just upgraded to Lion. Here's my unusual issue: Some of the emails I try to send using Apple Mail get rejected by my ISP's outgoing mail server ( I am required to use the ISP's outgoing server to send mail using password authentication). I can't seem to find any rhyme or reason as to when and why this happens. It is an "on again, off again" issue and occurs at different times to different email addresses I am trying to send to. Sometimes an email address is allowed to be sent to by my ISP. Sometimes it is not. When the message is disallowed, I get ths following error message:
"Sending the message content to the server failed. Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent."
I cannot send mail using any other outgoing server other than the one the ISP requires. About 95% of my messages make it through there.
Initially, I assumed the issue must be my ISP but I've tested the ISP's outgoing mail server using web mail and there is no issue there. I can also send web mail from my web hosting account. I am pretty sure Apple Mail is doing something to offend the outgoing mail server. Anyone have any ideas? This is very odd.

The symptoms you describe sound like an unstable Internet connection to me. Webmail and SMTP are two different things, so when web mail does work, that does not mean that you can connect to the mail servers through SMTP. Could be the Internet connection or a firewall. You should try to send the same mail, with the same outgoing mail server at different times, when that works once and does not work another time, it is very likely that this is a problem that only your ISP can fix, since no settings have changed...
Hope that helps

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From [email protected] Tue Sep 9 00:27:52 2008
Received: from p02c11m066.mxlogic.net (mxl144v245.mxlogic.net [208.65.144.245])
by host2.52601.com (8.12.11.20060614/8.12.10) with ESMTP id m894Rqa2031890
for <[email protected]>; Tue, 9 Sep 2008 00:27:52 -0400
Received: from unknown [207.172.157.102] (EHLO smtp02.lnh.mail.rcn.net)
by p02c11m066.mxlogic.net (mxl_mta-5.7.0-1)
with ESMTP id 84bf5c84.3171756976.300217.00-037.p02c11m066.mxlogic.net (envelope-from <[email protected]>);
Mon, 08 Sep 2008 22:27:52 -0600 (MDT)
Received: from mr02.lnh.mail.rcn.net ([207.172.157.22])
by smtp02.lnh.mail.rcn.net with ESMTP; 09 Sep 2008 00:27:52 -0400
Received: from smtp01.lnh.mail.rcn.net (smtp01.lnh.mail.rcn.net [207.172.4.11])
by mr02.lnh.mail.rcn.net (MOS 3.8.6-GA)
with ESMTP id PAK98602;
Tue, 9 Sep 2008 00:27:51 -0400 (EDT)
Received: from host-sse217.res.openband.net (HELO S0032027583) ([216.40.64.217])
by smtp01.lnh.mail.rcn.net with ESMTP; 09 Sep 2008 00:27:51 -0400
Reply-To: <[email protected]>
From: "R&R Traders" <[email protected]>
To: "PIERCE PAULA" <[email protected]>
Cc: <[email protected]>
Subject: WEAPON PAGE
Date: Tue, 9 Sep 2008 00:27:53 -0400
Organization: R & R Traders
Message-ID: <UENERkVCMDkAAQACAAAAAAAAAAAAAAAAABgAAAAAAAAAEyNd+5kkh06d3llPqgzVwsKAAAAQAAAAF/aL [email protected]>
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="=_reb-r1E746C67-t48C5FB48"
X-Priority: 3 (Normal)
X-MSMail-Priority: Normal
X-Mailer: Microsoft Outlook, Build 10.0.6838
Importance: Normal
X-MimeOLE: Produced By Microsoft MimeOLE V6.00.2900.5579
Thread-Index: AckSNGzaztKPqy6gS1+R4u4O72TkMA==
Disposition-Notification-To: "R&R Traders" <[email protected]>
X-Junkmail-Status: score=10/50, host=mr02.lnh.mail.rcn.net
X-Junkmail-SD-Raw: score=unknown,
refid=str=0001.0A010207.48C5FB47.01B1,ss=1,fgs=0,
ip=207.172.4.11,
so=2007-10-30 19:00:17,
dmn=5.4.3/2008-02-01
X-Junkmail-IWF: false
X-Processed-By: Rebuild v2.0-0
X-Spam: exempt
X-MAIL-FROM: <[email protected]>
X-SOURCE-IP: [207.172.157.102]
X-Greylist: Sender IP whitelisted, not delayed by milter-greylist-2.0.2 (host2.52601.com [65.108.5.169]); Tue, 09 Sep 2008 00:27:52 -0400 (EDT)
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I sent two different photos. The same photo has been placed in both boxes.
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Some email addresses won't send - sometimes.

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