Many mails bouncing specifically with attachments

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naikmanish
Posts: 24
Joined: Tue Aug 01, 2017 9:31 pm

Many mails bouncing specifically with attachments

Post by naikmanish »

Greetings,

I have a mail server configured, everything on the outside looks fine.

We send a couple of thousand emails every day from a particular domain. This server is for sending OTP and other transactional information to clients.

However, we have observed that emails that contain an attachment invariably do not reach the mail server. For e.g. if I mail from Yahoo/Gmail with an MS Word Document even of 50Kb the mail does not reach and yahoo/Gmail sends back this error. A Zip/Doc/Rar, I have tried all attachments.


Mail Text of Yahoo mail not reached.

Sorry, we were unable to deliver your message to the following address.

<user@mydomain.com>:
Unable to deliver message after multiple retries, giving up.

---------- Forwarded message ----------


Mail Headers from Yahoo

Received: from 10.213.170.250

by atlas201.free.mail.gq1.yahoo.com with HTTPS; Wed, 24 Mar 2021 02:06:47 +0000
Return-Path: <>
Received: from 66.163.187.147 (EHLO sonic316-21.consmr.mail.ne1.yahoo.com)
by 10.213.170.250 with SMTPs; Wed, 24 Mar 2021 02:06:47 +0000
X-Originating-Ip: [66.163.187.147]
Received-SPF: none (domain of sonic316-21.consmr.mail.ne1.yahoo.com does not designate permitted sender hosts)
Authentication-Results: atlas201.free.mail.gq1.yahoo.com;
dkim=pass header.i=@yahoo.com header.s=bounce;
spf=none smtp.mailfrom=sonic316-21.consmr.mail.ne1.yahoo.com;
dmarc=pass(p=REJECT) header.from=yahoo.com;
X-Apparently-To: naikmanish@yahoo.com; Wed, 24 Mar 2021 02:06:47 +0000
X-YMailISG: pcc18JwWLDsVGB_vqrNBsOlqBZZ9CoLO_tkOC8hYoT1P7EcY
USsSIa08VDSDhvdzs_GM7tlFSaEEcH30EYSO_EiOnZArYlF8VFzlRwZ7tZ7I
ogBo6Y0mso.PJmAiTdc.E0hP5GkiOoECjhgozEWVKvM0f12C_odxy1IZzsYE
dUOQH0.X3TRVUY7mKiT0Mv.QIZ0i02lA8Qa_gjVOHuTB.fiodjvhquzXm_wI
_xosUmtoW8rughY9MnSK2a06BcPJhALGQuQWjKEGAMVDMn7gL2mTyEJoFQ3h
K6.sKXYMfFt1ufWZQskZ0HzHwYFxJYrYfy0_RLJ8ymo.vapBJxbcRPJSc8nW
V3Bk4fAsQuEIKs4cybZoJgcRSNTWUzdMxvhrE9OoNZRUCEv0dkt8Uh.WXNh5
LAp2c4hywHH0_3EKqvFTZv6JzZJOKwy5NVX8A1wUXqq3WBkl2WPGnIDKfB7D
LHlz7CFEQVpCYQZYDEp9ZSBLYhYIgyUlxY6i52xVvNamWXEoD_nShs2vjnIo
aWKjCC1GewcakBDTw.IeIKA3c8QftkCDDJ83fCZCm3eYjZUyAq6YHWXfe5v5
BNkc21QJMqWVesxKbyqjUHLl2Ol7fHU5mddc_xeiENVehRuJiZKdmzBZE985
VCWaHKbiVc0.HpMrAK7QtZ5xrEC_Dmg2uAlpz8Betb1iUedGhbWpoZESeu3k
.oJkPRmurGc9EnkW0hKgk5fXcaEe0OvaFYpPmIhAXF7Bt5GQgCRDpr31NHeo
xIQ4Xo.hDweWfddHCJhLlfQNiBCwhcvPSw8gYv7rU2GK7sYYtCwcnnjmh4sp
TmnJ5nWNPG1EQPK467dADOJf8lXFz9uqmjKtqEiWckWwKV9PrkcGb.XYEpDW
ebpPW0QhS9_62SHpdu1EC3tlwAjbmHSkisIQSrsLJN3hL8wHm_XcKFR30xiz
_vR6nD21EZnH9V2SZQ2pyxWbzsLVbzjY1CqTmvoJd9g.SdZwqMgp6H8EoOwx
WT7fFzMnSRZ4kp3OkAIojjjZFzKn8P0AnJw3wT3qmpEFbUiyHy0rumRrzxhj
Wwvz_jUDQloiNhJZJyQXPsT8UWSsbG9Wk2q50kOsDMsLPpP7YU0w9rgmvBrP
WsmkX2GNrJrXw6_fOUi8L4di0yqwp6AL1AhrUYXwBb.ZLGqiyNmnGerxkYB8
Uvt85C0-
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=yahoo.com; s=bounce; t=1616551606; bh=yRMPUeLGB2hG7JN6dPic4r4cT+5K9EMIuJWiOR7Qkks=; h=Date:From:To:Subject:From:Subject:Reply-To; b=C90cXxiz+wmQOqu0vYxfb/qvqnngqSwIwuzhyoXxmQY42t6Nfb4gDzwWYmn0U9NZbxgEjq3IYNwMDbcbf9+RqaV0beZlzwTnX2jOGMUlqnR7w4JiWo53Vc+rhYDs+193kzv1Gylg0rDimTMAHP/N1wZbjUXoTNps7Q9s/2KAWxs=
X-SONIC-DKIM-SIGN: v=1; a=rsa-sha256; c=relaxed/relaxed; d=yahoo.com; s=s2048; t=1616551606; bh=bv3oXaY0Ck2m8XwqPRnAPVnDQ9n9/JRP0rOK68WwQok=; h=X-Sonic-MF:Date:From:To:Subject:From:Subject; b=fco9RJFaws3qZRUO3mkpT/Hj7hURmF550cJ0XBBcrjuYKCL7v0gil7Xge91/fI7rCPR0niPEKL84Bw2mEvbnAhOJGqI643/muqFQ4bxDtieOFDoUOIri+PJgGCs8Qv3+Jd02FwXEfaU6K0/ZFQ6jIkl33Yg2Rs3x9m2+IrguSrz/yUlXl9DhQMWlsOLNNxEERMSZxvNo7CsXJhoILxLf54etgOHPQdGYbm6mNXiiYqXb1UnLzkqh1vVd4z8UshnaYZwpGcatykbTW1b1mvEizGu4zfYeWszZ+zWnvwlhvLYs048lV4d5yXlIhqiAaFnO6uMC3iOkD27hnTppe4QFvw==
X-Sonic-MF:
Received: from sonic.gate.mail.ne1.yahoo.com by sonic316.consmr.mail.ne1.yahoo.com with HTTP; Wed, 24 Mar 2021 02:06:46 +0000
Date: Wed, 24 Mar 2021 02:06:46 +0000
From: MAILER-DAEMON@yahoo.com
To: username@yahoo.com
Message-ID:
<2007071317.849153.1616551606268@sonic316.consmr.mail.ne1.yahoo.com>
Subject: Failure Notice
Content-Type: multipart/report; report-type=delivery-status;
boundary="-=Part.cf501.7a3ad84adcb4502a.17861fbf7fc.29862b26d5419ce9=-"
Content-Length: 30737




I believe I may be missing some small setting somewhere.


Thank you in advance.

Warm Regards

Manish Naik

MailEnable-Ian
Site Admin
Posts: 9738
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Many mails bouncing specifically with attachments

Post by MailEnable-Ian »

Hi,

What is reported within the SMTP activity and debug log files? Are you routing external emails via a spam proxy/firewall?
Regards,

Ian Margarone
MailEnable Support

naikmanish
Posts: 24
Joined: Tue Aug 01, 2017 9:31 pm

Re: Many mails bouncing specifically with attachments

Post by naikmanish »

Greetings Ian,

We have a regular firewall/NGFW at the perimeter with NAT configured.

The SMTP activity and the Debug logs files are not having any flags.

Now to make sure that there is no external problem, I tried with mailenable enterprise on both sides. FYI, all three servers are in different locations around the world and the two server used for sending are production servers working since years.

Problem Explanation :

I sent email from
User@DOMAIN-ONE.COM
and
User@DOMAIN-TWO.COM

To

Receiver@DOMAIN-THREE.COM ( This is the problem mail server)


I could receive none of the email from both DOMAIN One and Two. Also the size of the attachment is merely 4-5 MB. Not too huge.

None of the sending email servers have any issues even in the Log Files.
Sample LOG :
Logs from DOMAIN-ONE Mail Server (I have changed all identifiable parameters please)

A.MAI 780 111.222.333.444 220 DOMAIN-ONE.COM ESMTP MailEnable Service, Version: 10.11--10.11 ready at 04/06/21 02:32:52 0 0
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 EHLO EHLO HOMEPC 250-DOMAIN-ONE.COM [111.222.333.444], this server offers 6 extensions 173 13
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 AUTH AUTH LOGIN 334 VXNlcm5hbWU6 18 12
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 AUTH {blank} 334 UGFzc3dvcmQ6 18 30 sender@domain-one.com
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 AUTH {blank} 235 Authenticated 19 18 sender@domain-one.com
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 MAIL MAIL FROM: <sender@domain-one.com> 250 Requested mail action okay, completed 43 36 sender@domain-one.com
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 RCPT RCPT TO: <receiver@domain-three.com> 250 Requested mail action okay, completed 43 34 sender@domain-one.com
04/06/21 02:32:52 SMTP-IN D06F13502B2A44A3B4C296BF2C9B0F0A.MAI 780 111.222.333.444 DATA DATA 354 Start mail input; end with <CRLF>.<CRLF> 46 6 sender@domain-one.com
04/06/21 02:32:56 SMTP-IN 8210D4ABA9D74443BA37F8F940CDA83D.MAI 780 111.222.333.444 QUIT QUIT 221 Service closing transmission channel 42 6 sender@domain-one.com


After the above log entry in the DOMAIN-ONE.COM (Sender Server) Email comes back with the following :

MailEnable: Message delivery has been delayed.

Message is waiting at DOMAIN-ONE.COM for delivery to DOMAIN-THREE.COM

The message will be retried for another 30 hours.

Reason: Mail server for domain-three.com could not be contacted at this time. MailEnable will keep trying to deliver this message and will notify you of any progress.


Message headers follow:

Received: from XYZPC([123.234.345.456]) by DOMAIN-ONE.COM with MailEnable ESMTPA; Tue, 6 Apr 2021 02:32:52 +0530
From: sender@domain-one.com
To: <receiver@domain-three.com>
References: <BDBD3E1F-16C8-44B1-8E69-B4D7BFDDE31E@DOMAIN-ONE.COM>
In-Reply-To: <BDBD3E1F-16C8-44B1-8E69-B4D7BFDDE31E@DOMAIN-ONE.COM>
Subject: FW: My PDF File Attachment.pdf
Date: Tue, 6 Apr 2021 02:32:40 +0530
Message-ID: <010c01d72a5f$0aaae2b0$2000a810$@DOMAIN-ONE.COM>
MIME-Version: 1.0
Content-Type: multipart/mixed;
boundary="----=_NextPart_000_010D_01D72A8D.246345C0"
X-Mailer: Microsoft Outlook 16.0
Thread-Index: AQGKmq9OkfeUuVzXlknYsi5d5gorBas/iKFg
Content-Language: en-in
X-Envelope-Sender: sender@domain-one.com
X-ME-Bayesian: 0.000000



Logs from DOMAIN-THREE Mail Server ( This is the problem email server)

I do not see any logs from sender@domain-one.com at all !


At the same time, I tried sending with gmail.com, the logs show that the email was received but the inbox does not show the message ?

The biggest problem is Random behaviour.
for example, I send am email from myusername@yahoo.com couple of times a day, sometimes it reaches and some of the emails dont reach! Therefore, we are unable to rely on the server to receive/send email. I mean, we cannot trust if the email we just sent will ever be received on that server !


Please let me know and I can send you the logs of both sending and receiving server on an email ID you designate as I cannot post here publicly.

Our License is under maintenance, but the local service provider/dealer has been of no help.

Thank you so much

Warm Regards

Manish Naik

MailEnable-Ian
Site Admin
Posts: 9738
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Many mails bouncing specifically with attachments

Post by MailEnable-Ian »

Hi,

Would need specific details of the domain names etc of all servers. Your best way forward here would be to lodge a support ticket and provide all the detailed information and log files.
Regards,

Ian Margarone
MailEnable Support

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