email bounce back while sending emails from Gmail with attachments =>1 MB

singh_vir
singh_vir used Ask the Experts™
on
i have an exchange 2007 server (hub and edge server setup ) . recently i have been encountering issues receiving emails from GMAIL account with attachments =>1MB . the same attachments get through if sent from an hotmail account . User receives a delay email after around 12 hours which repeats for the next 2-3 days and then a permanent delivery error messages is received . someone suggested disabling Chunking on the receiver connector should resolve this issue but i do not have this to effect the current flow of the emails .

Please advice !

bounce back email sample :

This is an automatically generated Delivery Status Notification

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipient has been delayed:

     vsingh@actionimpact.com

Message will be retried for 1 more day(s)

Technical details of temporary failure:
Google tried to deliver your message, but it was rejected by the server for the recipient domain actionimpact.com by mail.actionimpact.com. [91.75.176.148].

The error that the other server returned was:
421 4.4.1 Connection timed out
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The report is advising you that the mail delivery has been delayed because the destination server is not reachable.  Telephone your contact and advise them that their server is not accepting connections.

See how it is successfully resolving the MX record name to mail.actionimpact.com and giving the IP address?  Your server is successfully finding out how to contact them, but they are not answering when your server attempts to connect.

I am assuming that your server can successfully send to other e-mail address domains with no issues.

Author

Commented:
Hi , thank you for the reply . MX records seems to be correct . I can receive emails from almost all the domains except one which is sister company @ises-me.com but hosted separately. the user get the below bounce back almost 80 % while sending emails to actionimpact.com .

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:
 
  @actionimpact.com
    retry time not reached for any host after a long failure period

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:
 
@actionimpact.com
    retry time not reached for any host after a long failure period

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:
 
@actionimpact.com
    retry timeout exceeded

Issue 2 :

i can receive emails with and without attachments from almost all the domain ( except the one i mentioned above ) , but have issues receiving emails from gmail with attachment over 1 MB . i get the below error after 4 hours that the email has not been delivered :

Message will be retried for 2 more day(s)

Technical details of temporary failure:
Missed upload deadline (state SENT_MESSAGE)

Delivery to the following recipient has been delayed:

@actionimpact.com

Message will be retried for 1 more day(s)

Things i have done to resolve :

-           Disable chunking on recieve connector
http://social.technet.microsoft.com/Forums/exchange/en-US/aa66b02e-fae0-4366-a1e7-f99c2b961563/exchange-2007-is-not-accepting-or-timing-out-receipt-of-large-emailserror-returned-421-421-441?forum=exchangesvrsecuremessaginglegacy
 
 
-          Increase of connection timeout
http://www.petri.co.il/forums/showthread.php?t=42478
 
any help / support appreciated .

thanks
Hi,
Try changing the timeout setting on your server - see http://forums.msexchange.org/SMTP_Timeout/m_1800442922/tm.htm

Also read: http://www.petri.co.il/forums/showthread.php?t=42478

What I can think of is that Hotmail messages work well with your existing server settings and that Google settings dont.
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Author

Commented:
Hi ,

I have already updated the connection timeout to 20 minutes on both the receiver connector . Email with an attachment 2 MB goes through the setup successfully , but i receive an delay message if there is anything > 2 MB. The same emails sent from hotmail goes through successfully .   please advice if there are any other particular settings i need to verify for this issue .

bounce back email while sending 4 MB attachment using Gmail :

This is an automatically generated Delivery Status Notification

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipient has been delayed:

     vsingh@actionimpact.com

Message will be retried for 2 more day(s)

----- Original message -----

X-Google-DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
        d=1e100.net; s=20130820;
        h=x-gm-message-state:mime-version:date:message-id:subject:from:to
         :content-type;
        bh=FBsSqHrDhvWbLxqhJ9wJ2SdJeGWArQC89u4k83/dB8k=;
        b=drul5fK/XqDerM8dO+1rE34O1KgA6vQamyHOASUy++dqTZlOev7gaDiEjFh4opC16f
         OSC7ibuu44NoDMM/+fd/6T6a44oBxRUiUSIinaV+gCUn0o2AcFUvayDAl0sPaQwPm2VZ
         U/DvIEZai8ED/LKaV2EXtYNtUun91KlbPXNiZyuj0t0gSVQOvqEiNjR9M0pOvWyaTNEq
         91t1KbjD5+3AZTJXds4cRZEMWhLcrG2DT/o1BrySphkNQU8mF9eVdPZE4nNKStX2HT6W
         dRzJwO+5ExXwJTda6J6Gu0dWzVSP307m9BWmgVoWRFszCaPaWdBY62qUKnvdk0H0RrJn
         3BQw==
X-Gm-Message-State: ALoCoQntodgMd7TD/n7sdE4BdBa90xjRLbQr01jvMJCKclwTN0k3Gl3ynApOIjMVusSEWg5HI6gM
MIME-Version: 1.0


Thanks
When you increase the timeout, do those 1MB messages get received?

I would suggest that since you have most of the error reports and issue details, to contact Google support.

Google has an online support link or this type of scenario. Please visit https://support.google.com/mail/troubleshooter/2920052?hl=en and then proceed with the prompts. see if that helps.

Author

Commented:
Yes the one with 1 MB upto around 2.5 MB come in without any fail . Its just those emails with > 2.5 MB gets bounces back with a delayed delivery email .

will try the google support and update . Let me know if you have any other solution in the bag to test for this scenario .

Thanks
Ok. Also, check your server TLS Encryption section. Google uses it but I think this should not apply here.

Use a domain checker like the one found at www.dnsstuff.com to check your domain settings and pay specific attention to mail server related outputs. Might give you a heads up on any issues.

Author

Commented:
Thank you . I have tested the same using the online tool and do not see any specific issues .

Find attached the report .
dnsreport-actionimpact.com.pdf
Add the SPF record. You will need that in place.

Otherwise report looks okay to me too. Will await your feedback on what happens with contacting Google. The link I gave you directs you to an online contact form at the end. Give them as much info as you can to check on this.

Author

Commented:
Haven't received back any response from Gmail . But the latest bounce back emails have the below error message:

Delivery to the following recipient has been delayed:

     vsingh@actionimpact.com
Message will be retried for 2 more day(s)

Message will be retried for 1 more day(s)

Technical details of temporary failure:
Missed upload deadline (state SENT_MESSAGE)

any help would be much appreciated .

Thanks

Author

Commented:
another bounce back different from the ones received earlier


Remote Server returned '< #4.4.2 X-Postfix; lost connection with mail.actionimpact.com[91.75.176.148] while sending message body>'
Original message headers:

Return-Path: <elona.bytyci@dewa.gov.ae>
Received: from dewaserv773.dewa.gov.ae (unknown [127.0.0.1])
      by IMSVA (Postfix) with ESMTP id 358214C9122
      for <hgrimshaw@actionimpact.com>; Mon, 10 Mar 2014 11:00:02 +0400 (GST)
Received: by dewaserv773.dewa.gov.ae (Postfix, from userid 901)
      id 449952A085F; Mon, 10 Mar 2014 10:59:41 +0400 (GST)
Received: from dewaserv773.dewa.gov.ae (unknown [127.0.0.1])
      by IMSVA (Postfix) with ESMTP id 7A4A54C802B
      for <hgrimshaw@actionimpact.com>; Sun,  9 Mar 2014 10:59:21 +0400 (GST)
Received: from DEWASERV625.dewa.gov.ae (unknown [10.12.200.237])
      by dewaserv773.dewa.gov.ae (Postfix) with ESMTP id 0F5634C8008
      for <hgrimshaw@actionimpact.com>; Sun,  9 Mar 2014 10:59:21 +0400 (GST)
Received: from DEWASERV624.dewa.gov.ae (10.12.200.236) by
 DEWASERV625.dewa.gov.ae (10.12.200.237) with Microsoft SMTP Server (TLS) id
 15.0.712.24; Sun, 9 Mar 2014 10:58:25 +0400
Received: from DEWASERV624.dewa.gov.ae ([10.12.200.236]) by
 DEWASERV624.dewa.gov.ae ([10.12.200.236]) with mapi id 15.00.0712.012; Sun, 9

Author

Commented:
Hi ,

i have restarted the firewall ( ASA5510 ) and cross checked if there was a esmtp policy enabled .

Please advice if there are any other trouble shooting steps for the issue .

Bounce back :
Hi. This is the qmail-send program at cinchhosting.com.
I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.
 
Connected to 91.75.176.148 but connection died. (#4.4.2)
I'm not going to try again; this message has been in the queue too long.


Delivery to the following recipient has been delayed:


Message will be retried for 2 more day(s)

Technical details of temporary failure:
Missed upload deadline (state SENT_MESSAGE)

Author

Commented:
Any assistance on the same . Has someone experienced this issue earlier ?

i have received the below bounce backs :

Error messages / bounce backs :

*Bounce back for emails from gmail and few other domains with attachments > 2 MB
Technical details of temporary failure:
Missed upload deadline (state SENT_MESSAGE)

*Emails not hitting the exchange server as the sender do not receive any bounce back emails .

*Connection timeout bounce back emails
retry time not reached for any host after a long failure period
retry timeout exceeded
*Connected to 91.75.176.148 but connection died. (#4.4.2)
I'm not going to try again; this message has been in the queue too long.
Thank you evenyone for the assistance and advice.

unfortunately the issue was with the service provider blocking emails under their spam filters .

Thanks

Author

Commented:
Solution found with the service provider .

Thanks

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