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Email delivery (incoming) issues. Never makes it through

Posted on 2013-01-09
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Last Modified: 2013-05-02
A few of our users have been getting their mail blocked (incoming) from a particular source.  It may be by more, but they’ve gone unnoticed thus far.  Below is a copy of the fail report the sender received as well as the log sessions from my server.  From what I can tell, it seems to be either falling off at our local server, or at  exchange.  I base that off the “failed in remote data – psmtp”

did not reach the following recipient(s):

bb@bb on Thu, 3 Jan 2013 14:33:57 -0500
   The e-mail system was unable to deliver the message, but did not
report a specific reason.  Check the address and try again.  If it still
fails, contact your system administrator.
   < mx2.ppdi.com #5.0.0 smtp; 5.4.7 - Delivery expired (message too
old) [Default] 451-'Failed in remote data - psmtp' (delivery attempts:
71)>
Reporting-MTA: dns; RTPMAIL01.americas.ppdi.local Final-Recipient: RFC822; bb@bb Action: failed Status: 5.0.0 X-Supplementary-Info: < mx2.ppdi.com #5.0.0 smtp; 5.4.7 - Delivery expired (message too old) [Default] 451-'Failed in remote data - psmtp' (delivery attempts: 71)> X-Display-Name: bb@Bb

I tracked the log files down and see the failures on our server end over, and over again for this one message which kept trying to deliver from  Dec31-jan 3rd where it ultimately gave up.

64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 <<< MAIL FROM:<prvs=70595fde5=cc@cc>
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 >>> 250 2.1.0 <prvs=70595fde5=cc@cc>... Sender ok
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 <<< RCPT TO:<dd@dd>
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 >>> 250 2.1.5 <dd@dd>... Recipient ok
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 <<< RCPT TO:<ee@ee>
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 >>> 250 2.1.5 <ee@ee>... Recipient ok
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:11 -0700 <<< RCPT TO:<bb@bb>
64.18.1.138     [00000E2C] Mon, 31 Dec 2012 12:31:12 -0700 >>> 250 2.1.5 <bb@bb>... Recipient ok
SYSTEM          [00000D18] Mon, 31 Dec 2012 12:31:12 -0700 Client session DNS server at-file-01.a.com issuing MX query for "a.microsoftonline.com"
64.18.1.147     [00000C64] Mon, 31 Dec 2012 12:31:12 -0700 >>> 250 2.6.0 285971 bytes received in 00:00:06; Message accepted for delivery
64.18.1.147     [00000C64] Mon, 31 Dec 2012 12:31:12 -0700 <<< QUIT
64.18.1.147     [00000C64] Mon, 31 Dec 2012 12:31:12 -0700 >>> 221 2.0.0 mail.a.com closing connection
SYSTEM          [00000C64] Mon, 31 Dec 2012 12:31:12 -0700 Disconnected
SYSTEM          [00000D18] Mon, 31 Dec 2012 12:31:12 -0700 Client session DNS server responded with 0 (OK) [1]
SYSTEM          [00000D18] Mon, 31 Dec 2012 12:31:12 -0700 Client session Connecting to "mail.global.frontbridge.com"

I am not positive that’s all from that one message or if I copied too much.  That message leads me to believe this email made it through Postini, to our server and then off to you at exchange.  Shortly after, this is the log error that repeated itself for 3 days…

64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:09 -0700 <<< MAIL FROM:<prvs=70595fde5=cc@cc>
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:09 -0700 >>> 250 2.1.0 <prvs=70595fde5=cc@cc>... Sender ok
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:09 -0700 <<< RCPT TO:<dd@dd>
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:09 -0700 >>> 250 2.1.5 <dd@dd>... Recipient ok
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:09 -0700 <<< RCPT TO:<ee@ee>
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:10 -0700 >>> 250 2.1.5 <ee@ee>... Recipient ok
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:10 -0700 <<< RCPT TO:<bb@bb>
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:10 -0700 >>> 250 2.1.5 <bb@bb>... Recipient ok
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:15 -0700 <<< DATA
64.18.1.61      [000010CC] Mon, 31 Dec 2012 12:39:15 -0700 >>> 354 Enter mail, end with "." on a line by itself
SYSTEM          [000010CC] Mon, 31 Dec 2012 12:44:18 -0700 Disconnected


We have an annoying mail delivery setup which I will be changing once we get through a project we're on right now.  But, right now incoming emails shoot though Postini/Spam-x 1st, then they come through our building to our local Merak mail server then off to Microsoft where exchange handles the rest.  Yes, annoying.
The emails clearly seem to make it past Postini, to our local server as I see the attempts over and over.  but the "failed in remote data" and the "354 end with a period" errors are throwing me for a loop and I cant figure out the fail point.

FYI.. the emails are only being lost if they have an attachment (and then again, only some of those).  Emails from the same sender without attachment are fine.  The attachments are only very small excel spreadsheets.
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Question by:papo08
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Expert Comment

by:Manpreet SIngh Khatra
ID: 38762541
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by:papo08
ID: 38807969
Yes, I mentioned that our email goes through Postini in the above message.
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papo08 earned 0 total points
ID: 39117631
after a lot of work with MS, they have determined they are at fault and they have to wor kwith me on a duplicate server in their system that is causing this issue.
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Author Closing Comment

by:papo08
ID: 39131080
MS has claimed the problem to be theirs.  awaiting solution
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